Blind item: Who is the ‘movie star’ who had an affair with Jessica Simpson?

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Before Prince Harry’s Spare broke records, Jessica Simpson was the unexpectedly successful memoirist of this generation. She wrote Open Book, which was published in early 2020 to rave reviews and great sales. It was the perfect blend of confessional, celeb gossip, substance abuse and real-girl sh-t. It established Jess as a writer, and now she’s written a short story for Amazon Original Stories. The story is called “Movie Star” and it’s about a brief affair she had with a super A-list movie star in the early ‘00s. She tells People Mag now: “I will tell you this… he is still a movie star!” OMG.

She met this guy at the 2001 MTV VMA after-party at Man Ray when she and her future husband Nick Lachey were on a break. She and Nick got back together and married, but they separated again and soon after, she began an affair with this Movie Star. Hilariously, at this exact moment in September 2001, she writes that she was being pursued by two different boy banders, one from *NSYNC and one Backstreet Boy. Here’s an excerpt from the exact moment she meets the Movie Star:

I didn’t know that night at the MTV party that I was exactly five days away from going back to Nick and eventually marrying him, but that’s another story. For now, picture me in the black cocktail dress, doing what I was told to do by Columbia Records. Tonight was part of my job—to get as much press as possible for my new single “A Little Bit.”

The party on the red carpet got so crowded that we were all on top of each other, and my security guard stopped me from falling when I got jostled. I was determined to stand my ground, because my bosses at Columbia Records had told me, “We want you on the red carpet.” I truly thought that meant I was supposed to keep at least one foot on it at all times. My new album, Irresistible, had just come out, and these men sitting at the executive table had said it would define me— even as they had refused to let me write any of the songs on it. They scolded me to get down to 102 pounds, and they dictated my hair’s exact length (past my shoulders) and color (keep it blonde). If they knew I was avoiding another famous boybander, they would not be pleased. That much I knew. Dating a famous boybander would bring them the headlines they wanted.

As the phone kept ringing in my bag, I gave up my spot. “Should we go to the bar?” I asked my security guard. “I’m 21 now. I can buy a drink.” He grimaced, and I wasn’t sure if he disapproved of the drink or the calories. He happened to also be my trainer. I think he was paid to be there more to protect me from the hors d’oeuvres that were being passed around than crazed stalkers, but I liked him.

I saw his face suddenly brighten at someone behind me, and I turned to see the packed crowd somehow parting as a massive movie star walked toward us in jeans and a T-shirt. My bodyguard had said they were friends, but I’d wondered if he had maybe been exaggerating. Judging by the clenched handshake bro hug, the love was real. “This is Jessica,” my bodyguard said.

“I know,” said the Movie Star. He gave me a different hug; a modified celebrity embrace he held a few seconds longer than I expected. As our mutual friend, my bodyguard talked, this megastar, who I grew up thinking was so hot, eyeballed me up and down. Like he was undressing me with his eyes, which was fine because I had plenty of reasons to ditch that outfit and change.

Movie Star started on small talk, and as he leaned in, I had the presence of mind to know, Oh, this is what it’s like to be hit on. Because, other than my ex-boyfriend, no man had ever been so upfront about looking at me in a provocative way. At least that I wanted to look at me that way. He placed a hand on my hip and leaned in so I could hear him better. Only he talked even softer.

I felt a funny feeling. I watched his lips move, but the rest of the world was in a dreamy focus. I was a big reader to make up for dropping out of high school, so I had read enough of Jane Austen and the Brontë sisters to know what was happening. This wasn’t love, but it was something dreamy. This is what they talk about when they talk about swooning, I thought. This is one of those swoon moments. This was different than the guilty butterflies that boys my age brought on when I thought something might be possible. This was real.

And I wasn’t ready. I fled Movie Star. I made some excuse and acted like Cinderella in bad booties. I wish I could say I was playing it cool. I later found out this was seen as “playing hard to get.”

[From People]

Jessica did get his number, and then five years later, after her marriage to Lachey crashed and burned, she reconnected with the Movie Star. She kissed him at the Beverly Hills Hotel and she was very hot for him. They would hang out in nightclubs, at mutual friends’ houses and even a movie set. He told her that things were winding down with his then-girlfriend, but Jessica came to realize that she was the side chick and he was hiding her. She writes that she felt “like a call girl” who was only there to have sex with him.

So, this is a Blind Item… who is the guy? She says she grew up watching him, so let’s be somewhat generous and say that he should be at least ten years older than her? She’s 42 now, so someone at least in their late 40s now. I totally looked up photos from the VMA after-party in 2001 to see if there were any movie stars photographed…um. Liev Schreiber was there!!! OMG, he has a thing for blondes too. Tim Robbins was there. Jessica has her photo taken with Derek Jeter! Anyway, I’m calling it… it was either Tim Robbins or Liev Schreiber. I’m leaning more towards Liev, so help me God.

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169 Responses to “Blind item: Who is the ‘movie star’ who had an affair with Jessica Simpson?”

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  1. Nightshade says:

    I don’t know much about Liev Schreiber, but he’s always given me complete dick vibes.. am I hitting the nail on the head or is he actually known as being a pretty cool guy?

    • Gah says:

      Liev basically hung outside my kids preschool in NYC waiting for me (a tall blonde) to emerge under the guise of walking his dog. This was when he was on a break from his current LTR who is a delightful woman. I am married and he knows it. I think he’s a good father. And like many actors likes to use his fame to get things he wants.

    • ProfPlum says:

      Liev’s kid was in my kid’s class. His girlfriend was so age-inappropriate. It was insane. She was barely in her 20s. And, yes, he totally walked around with huge BDE. Naomi was much more down to earth and low-key… and she and Billy Crudup always seemed like normal parents.

  2. Blue Nails Betty says:

    Was Liev a “massive movie star” in 2001? I hadn’t heard of him until later.

    • Josephine says:

      No. In 2001 it was the usual suspects, like Tom Cruise, Brad Pitt, Eddie Murphy, Bruce Willis, Denzel Washington, George Clooney, Mel Gibson. Sean Michael Scott was big then but too young I think? But if you’re talking megastar, there were not then many men who were huge box office stars.

      • Yvette says:

        Everyone is overlooking child stars that Jessica could have grown up crushing on. My two candidates are Ben Affleck (who would have been 29 in 2001, and whose big breakout film was “School Ties”–1992) and Leonardo DiCaprio (who would have been 27 in 2001, and whose breakout film was “What’s Eating Gilbert Grape”–1993).

      • Gabby says:

        My money’s on Affleck

      • Kimmy says:

        My immediate thought was Leo. I mean, come on…..

      • Yvette says:

        @Kimmy … 🙂 I know, right? Jessica was definitely in Leo’s wheelhouse–21, blonde, pretty, thin. And he is SO still a major star.

        @Gabby … But Ben was also in his ‘horndog’ phase as well. 🙂

      • Mariana says:

        Mark Walberg was wearing jeans and a t shirt at the 2001 vmas . He was a bad boy I could totally see him look her up and down like that and lie about having a girlfriend

    • Green girl says:

      Liev had been in the Scream films by that point but I don’t think even that would have been enough to call him a massive star in 2001. Is he even considered a list today? If it is him it’s weird to me that she said she grew up thinking he was hot. The first scream film came out in like 1996 so Jessica would have been about 16. To me that’s not what you would say if you only started watching someone’s films in your mid teens.

      I think it would either have to be someone much older.

      Edited because I misread the original text

      • Sarita says:

        Leonardo. She would have been in the age group to romanticize him from Titanic and Romeo and Juliet, and he was with Gisele during those years.

    • Kitten says:

      Nah he definitely wasn’t. TBH, if you ask a lot of people now who Liev Shreiber is, they won’t know. Plus, he’s attractive but definitely not her type.

    • Susie Q says:

      I agree, Jessica would not have ‘grown up’ watching Liev in movies. Gotta be someone else, just because there’s no pic doesn’t mean she didn’t talk to others.

      • Mariana says:

        Mark was the top earning actor just a few years back and he’s still big too tho and he was wearing jeans and a t at the vma

    • Leslie says:

      No, he wasnt….maybe Luke Wilson?

  3. Tecla says:

    Marky Mark

    • Lady Baden-Baden says:

      Yes. Other sites saying Marky Mark. A few suggesting Tom Cruise… but that’s less likely let’s be honest!

      • Christine says:

        Tom Cruise gives me asexual vibes. He doesn’t seem like the type that would be this forward.

      • Yep says:

        Think Mark W is a better guess than Liev or Tim Robbins.

        Also can imagine him doing this overt seduction routine to give the impression the woman’s the only one for him.

    • Leanne says:

      Definitely Marky Mark

      • Frippery says:

        FWIW, Mark W. would have had 2-3 young kids at home with his now wife during the hook up period Jessica is talking about. Which, it happens, but it puts the story in a much different light if it -was- him.

      • Juliette says:

        Oh I definitely believe that. I have a friend who was a driver in LA around that same time. He told me was called to a house to pick up someone and take them to LAX, at the crack of dawn. When he arrived, Jessica Alba came out with her bags, followed by MW. I assume it was his house because only JA went to the airport and he stayed behind. As my friend was helping with the luggage, MW got in my friend’s face and told him if he said anything about “this”, he’d get him fired from the car service. The only reason my friend mentioned it was because MW was a complete jerk. Otherwise I doubt he would’ve mentioned it (he drove celebrities around all the time, in LA no one cares ). Anyway long story short, definitely MW in my opinion.

      • Yep says:

        Thanks for the goss, Juliette.

    • Michael says:

      I agree that Whalberg is just the kind of ass who would hit on her and cheat on his GF and be bold about it. Also fits because he was a rapper/underwear model before and Jessica probably saw him in his Calvins when she was very young. I cannot stand the man but I could see her liking him

    • Moneypenny424 says:

      I just dug through pics and immediately knew it was Marky Mark! Kind of happy to see others agreed with my sleuthing 🙂

    • whatWHAT? says:

      eh, I wouldn’t consider MW an A-list movie star in 2000-2001…or NOW, really.

      def famous, but I’d go with Affleck or Leo over MW. Both of them were A-list then and now.

      • Annalise says:

        Marky Mark seems like the kind of guy who would be tight with his trainer. He definitely cultivated the image of “tough yet talented guy from South Boston who still kicks it with the friends he grew up with (and his trainer).” the operative term is “cultivated”.
        Also I could see him as the type to NOT want to hang out with people more famous than him. He wants to be the biggest star in his “crew”.

  4. LooneyTunes says:

    Did Brad Pitt go to that event? This sounds like Brad Pitt and he’s the only one whose career is still hot.

  5. Lauren R says:

    Google Mark Wahlberg VMA 2001. HE is wearing Jeans and a T shirt

    • CJW says:

      So was Will Smith

    • Mga_nyc says:


    • Kitten says:

      This is the best guess but I still don’t see how she can claim that she grew up watching him in movies. She’s around my age and that dude’s career was just starting when we were basically already young adults. I guess she was 15 when Fear came out but I’m still not thinking of him as some Big Epic Movie Star back then…or now, really lol.

      • Becks1 says:

        yeah I don’t think Mark Wahlberg was a “Big Movie Star” in 2001. By that point he had only been in a handful of movies as a lead (Fear, Boogie Nights) and I feel like it wasn’t until Planet of the Apes (2001) and Italian Job (2003) that he became cemented as a Movie Star over a rapper.

      • Kitten says:

        Exactly. It was when he started doing the big budget stuff that his career started taking off.

      • Jay says:

        For what it’s worth, she just says she thought he was “so hot” growing up – not necessarily that he was in movies when she was young. Marky Mark would have been all over the tv and in teen magazines when Jessica was growing up. I think her perspective might also be coloured by him being a “big movie star” now, not necessarily that he truly was then. Or, considering her relative naivety, maybe everyone she met that night seemed like a big star.

      • Maddie says:

        She didn’t say she grew up watching his films, she said she grew up thinking he was hot! And he was hot as Marky Mark!

      • Becks1 says:

        Yes I said below she would have grown up knowing him, but I don’t think anyone would have classified him as a “massive movie star” who could part crowds on a red carpet in 2001 or a “megastar” etc. If she had just said it was someone famous I would be 100% on board the “it was Mark Wahlberg” train.

        (I also completely think he’s the type to cheat.)

      • Trose says:

        It is 100% not Liv Schriber. I went to Jr High with Jessica, and I can assure you she was not the Liv Schribers brain is so sexy kinda (just north of) Dallas Tx kinda girl. Stuck up? Yes. But not that kind of stuck up.

        That’s the other thing. She’s not “from Dallas” at all. Very much the burbs. Road on a summer (I think science) camp bus one year with Ashley daily. She was such a funny spunky little girl. I was a few years older but I still thought she was super fun and funny.

        K, there is my download of Simpson girls.

        Def not Tim Robins cuz of the whole married at the time kinda thing and this would be a better story if said A lister was married to Susan Sarandon at the time.

        I hate to admit Marky Mark lines up. I’m so disappointed.

    • Jessica says:

      I’m almost exactly Jessica’s age and I grew up thinking Marky Mark was dreamy, good vibrations started the obsession lol, then he did Fear and his movie career took off, he’s still a huge star today so I think it’s totally possible. He doesn’t seem like the type to cheat but I can definitely see him looking someone up and down like that.

      • Ameerah M says:

        He TOTALLY seems like the type to cheat. He calls himself a devout Catholic and yet had ALL of his children out of wedlock before finally marrying their mother. He once talked about having sex and then immediately getting up and praying for forgiveness. He’s a hypocrite.

      • Jessica says:

        I have a terrible picker when it comes to men so you’re probably right on the cheating!

      • Christine says:

        He also seems to bro crush on every personal trainer he comes across. I was a Whalburgers fan, there’s lots of trainer bromance with this man.

  6. Blue Nails Betty says:

    Maybe Ben Affleck? He was huge in 2001.

    Or maybe Matt Damon?

    • Blue Nails Betty says:

      After reading other posts and googling I’m firmly on the “it was Marky Mark” team. He was huge in 2001, was known for being super physically fit (prolly how he knew the bodyguard-fitness pro), and he wore a tshirt/jeans combo at the event. Also, I have no doubt he’s cheated on his then girlfriend/later wife so he would want this kept quiet.

    • Susan says:

      I say it’s Affleck

  7. Noki says:

    Well she says he was wearing a t shirt and jeans, and I don’t think Liev was an A lister in 2001,he is barely one now. And late forties is rather young, he must be in his 50s possibly pushing 60 at this point.

  8. Leena says:

    Oohhh! Ding ding ding on Marky Mark! Except was he HUGE yet? I just don’t think Liev or Tim Robbins would be someone Jessica grew up thinking was hot, yknow? Lol, was Tom Cruise there? 😂

    • Blue Nails Betty says:

      Marky Mark was huge in 2001.

      • Jessica says:

        I remember him being huge when I was in high school and I’m Jessica’s age, not the big star he is now but he was definitely well known by teen girls!

      • Kimmy says:

        I graduated high school in 2003. Got my first laptop for college in Fall 2003. Marky Mark in his Calvins was my background screen. So def possible!

      • Christine says:

        It’s like there’s not a fan of NKOTB, in all of the CB land.

        Mark Wahlberg was a sex symbol when I was graduating from high school in 1993, by proxy of his big bro Donnie, and his body, and the underwear ads.

    • Becks1 says:

      No, he was not huge as a movie star in 2001. She would have definitely known who he was, and probably grew up with a crush on him, but wasn’t a Big Movie Star in 2001.

    • FHMom says:

      Tom Cruise was there, but not dressed in jeans

    • Concern Fae says:

      One thing I’ve learned from observing writer friends is that if you are competing in the same business, you see any success as big success. Someone who is working and financially rewarded for it is a big deal, even if people outside the business see them as meh.

    • Leslie says:

      Johnny Depp

  9. girl_ninja says:

    I sure did go to the Google machine and looked up the 2001 MTV VMA photo’s but I don’t have a clue. Maybe Mark Wahlberg, cause all I saw was Tom Cruise, the Rock, Hugh Jackman and Jim Carrey. They are still big actors, give or take Mark and Jim. Let me go and read Jessica’s original story.

    • Green girl says:

      Ok I’m voting for mark or tom, but I wouldn’t exclude The Rock. I don’t think Hugh was well known until Jessica was almost 20. I just don’t see her thinking Jim was hot at that time. Funny and popular sure, but I don’t think there were many teens who saw ace Ventura and thought he was hot.

  10. Milsevelt says:

    It’s Marky Mark 100%

    • Mabs A'Mabbin says:

      Imma go with Marky as well.

    • Twin Falls says:

      Yep. Dude gives total creeper vibes. And it tracks that he’d be good friends with an LA trainer/bodyguard.

    • L84Tea says:

      I 100% think it was Marky Mark. He was huge in 2001–he’d already done Boogie Nights and was getting firmly established as Mark Walberg the serious actor instead of Marky Mark, the pants dropping goober (anyone remember Eminem making fun of him and taking jabs at him on TRL?). And being friends with the bodyguard dude, yep, totally sounds like him.

  11. Tina says:

    Whoever it was, had a girlfriend (not wife, not single) in 2006. That’s a notable clue.

    • Imara219 says:

      Good call! Hmm, now I wonder out of the names mentioned. Marky Mark would have made sense but he was married in 2006, unless Jessica is flubbing a bit. With the current facts it’s either The Rock (he was divorced around 2006 I believe), Jim Carrey but I just don’t see him going for Jessica. Tom Cruise (hard read in this situation).

      • Lizzie Bennett says:

        I’m thinking Jim Carrey – that fits the grew up watching his movies part. Plus, Jim has a history with blondes: Jenny McCarthy, Lauren Holley, Rene Zellweger.

      • Imara219 says:

        I know Jim Carrey is really into blondes. Wasn’t he freshly broken up with McCarthy in 2006? Can’t quite remember. I forgot he was with Rene. My original thinking was that he usually went with tall women but you are right, Lauren Holley (his longest relationship at that time) was with a short woman and same with Rene. Maybe it’s him. I just don’t see an 2006 Jessica being enamored by Jim. This is some good gossip and fun 😀

      • Elizabeth Kerri Mahon says:

        Marky Mark got married in 2009.

      • Snoozer says:

        I just googled and he didn’t marry Rhea until 2009…

  12. Lucy2 says:

    Will Smith , Will Ferrell, Ben Stiller, Mark Walberg were also there. My guess is Mark (blech) and the time frame of his girlfriend/wife lines up.
    Plus the jeans and T-shirt thing. I put my money on him.

  13. Jennifer says:

    If she “can’t” say who it was, I don’t care.

    • Gobo says:

      I mean you’re on a gossip site with a massive focus on speculation, sooooo… O.K.

      • Jennifer says:

        ….Yeah, good point. I don’t find her interesting anyway though 😛 I was thinking “she hints about it but doesn’t say” kinda makes me wonder if she’s making it up. But looking at what people are citing about Marky Mark, perhaps not.

    • Jessica says:

      He probably has children and a wife at this point, he may have even married who he was with at the time he was cheating with Jessica, I respect her for not announcing and ruining lives 22 years later lol

      • Jesma says:

        I don’t think it was Marky Mark. He would have had a live in partner with kids. Very close to being married. Jessica makes it sound like he had a girlfriend whom he perhaps was playing off as not that serious.

      • J says:

        I think it is important for a betrayed partner to always have the truth. No matter how painful. You can’t consent participate in a shared life and with a sexual partner who is an unknown. Truth first always. I have been betrayed and it’s so crucial to know your own life and reality.

      • Claire says:

        Definitely Mark Wahlberg. The ages like up and he is 100 percent her type – his style is pretty similar to Nick Lachet. Also people have found a picture of what he wore to the 2001 music awards and it lines up with her description. I think she would have grown up with a crush on him absolutely.

  14. Sally’s says:

    Movie stars at the vmas 2001: Christopher Walken, Ben Stiller, Will Smith, Russell Crowe, George Clooney, Joaquin Phoenix, Hugh Jackman, Brendan Fraser, Mark Wahlberg, Jack Black, Will Ferrell, Jamie Foxx ,Tom Cruise, Morgan freeman, John Travolta, Jim Carey, 2 Wayans bros, Samuel l. Jackson, Brad Pitt. etc

    • Chaine says:

      Lol, trying to picture a hot secret romance between Jessica Simpson and Christopher Walken.

      • Ang says:

        Walken! OMG, she wishes. He’s my #1.

      • KimmyChoo says:

        This comment needs more cowbell! 🙂

      • TheVolvesSeidr says:

        @Ang “nostrovia – to Nick!” <3

      • Christine says:

        I need to start writing fanfiction, for the first time in my life. Jessica Simpson and Christopher Walken would be the most hilariously obtuse coupling on the planet. He would say something like, “It was an off day, that one day….” and she would suggest pool floaties, as an answer.

    • MF says:

      Well, we can eliminate John Travolta and Jim Carey. They’re still movie stars, but they are basically retired.

      I don’t think the Wayans Bros are A-listers. Walken and Freeman are probably too old–her description makes him sound younger.

  15. Jay says:

    No idea on the “movie star”, but this made me laugh when she talked about the red carpet: ”I truly thought that meant I was supposed to keep at least one foot on it at all times.”

  16. Whomever says:

    Wasn’t Mark Wahlberg and his circle the inspiration for Entourage? Kind of fits with him being so friendly with her bodyguard.

  17. J says:

    Ugh I’m so disgusted that she was an other woman. I thought she was the kind of woman who wouldn’t tear another down. :-(. So sad.

    • JesMa says:

      I don’t think this counts as other woman. It seems like her told her he was breaking up with a non-serious girlfriend. It seems like she later figured out she was just being used as a side chick. That happens all the time. When men lie about their relationship status. There are even loads of married men on hookup apps.

      • J says:

        But he didn’t tell her he was done w his girlfriend completely and said he felt sinful being with her?

      • JesMa says:

        Oh, I didn’t read the whole story just what they said here about her realizing she was a side chick. He said sinful? Hmmm that makes me even more curious about who it is.

    • AMA1977 says:

      How about don’t make the young woman (and in this case, one who was devalued by virtually everyone for everything except her looks, sold for entertainment in a salacious and damaging way by her father, and had just left a difficult marriage that was her first adult relationship) responsible for the man’s choices? HE had a responsibility to end HIS relationship cleanly before pursuing her. You talk about her “tearing women down” and then…tear her down by holding her to a standard you’re not holding him (the person with more power AND the person who is cheating) to.

      • J says:

        i think cheaters and side pieces are equally bad. I don’t give other women/men a pass – they are just as culpable. they hurt and tear down the betrayed partner just as much or almost as much as the person responsible to their official spouse or partner.

        If you know you’re encroaching on someones’s monogamous partner you are being just as terrible.

        I’m not counting people who have literally no clue they are side pieces

        And I’m not holding anyone to another standard. I hold the same standards. She doesn’t name the guy so I don’t know who she is talking about. For me it goes without saying he’s awful too.

      • Foff says:

        Well said, Ama1977. Thank you.

      • Christine says:

        Slow clap, AMA. You are exactly right, and I’ve done it with my previous comments, and I am sorry.

      • shanaynay says:

        @J says:

        Agree with you 100%

  18. TIFFANY says:

    I thought it was Colin Farrell. The time frame fits as he was the FB to young actress and pop stars.

    Was he at that party?

    • Becks1 says:

      I don’t think Colin Farrell was a huge movie star in the US in 2001.

    • Lala says:

      I bet it’s Ryan Philippe or Colin Ferrel. Not sure how to spell either. Definitely not Tom, Tim (really?!), Walken, or any other old dude. Come on. Ben I could see because he is a douche bag but Matt? No way. However it could all be made up for a book she’s selling.

  19. Sass says:

    Gotta be Mark Wahlberg. Ugh, he’s such a slug.

  20. Frippery says:

    Dammit, where is that Kris Jenner “This is a case for the FBI.” gif when you need it

  21. Becks1 says:

    I’m surprised more people aren’t focusing on Tom Cruise. Katie Holmes is less than 2 years younger than Jessica, so we know he wouldn’t have had an issue with the age gap. That’s 100% someone she would have grown up watching and thinking he was hot etc.

    my only sticking point is that he married Katie Holmes in 2006 when Jessica says he had a girlfriend, but maybe that’s what she meant when she said that she realized she was just a side chick.

    • Becks1 says:

      In looking back at what she writes – she called him a “massive movie star” who could part the crowds on a red carpet, and then later a “megastar” who is still a big movie star today. There are very few people who fit that bill. I think it had to be Tom Cruise. Brad Pitt doesn’t entirely fit bc he and Jennifer aniston were married at that point, and Shiloh was born in 2006 so that doesn’t fit with the idea of the relationship winding down.

      • Anners says:

        Tom Cruise and Brad Pitt were the two James that sprang immediately to mind as men who could part a sea of people. Leaning towards Tom Cruise, although he doesn’t seem like someone who enjoys sex tbh.

      • Nick G says:

        And Tom had left Nicole earlier that year.

    • The Old Chick says:

      My first two thoughts : clooney or Pitt. Pitt was with jolie about then. Could MW part a red carpet?

    • Becks1 says:

      Also sorry meant to say that Jessica is less than 2 years younger than Katie. Katie was born in 78, JS in 80. (I googled lol.)

    • Green girl says:

      Tom and Katie were married in November 2006, so if Jessica hooked up with Tom any time earlier that year then katie would have technically been a girlfriend (although she and Tom were engaged). Maybe Jessica is stretching the truth by using girlfriend instead of fiancée. Otherwise it might be too obvious for that timeline.

    • JesMa says:

      Tom doesn’t have enough game to make anybody swoon. He is awkward and unsexual.

      • Becks1 says:

        Did we realize how asexual he was in 2001 though? remember this is pre-Katie Holmes and the couch jumping etc. I could see Simpson being starstruck by him in 2001.

      • JesMa says:

        I always thought of him as unsexual. I remember those rumors about him needing to be coached on sex scenes with his own wife on the Eyes Wide Shut movie. He was famous and I guess many found him good looking, but I don’t know about sexy.

      • Sam says:

        But Cher gave his Performance a good Rating …

  22. ElleE says:

    Russell Crowe won an Oscar in 2001 for A Beautiful Mind and cheated on Jennifer Connelly openly.

    This is how he moves:
    “Because, other than my ex-boyfriend, no man had ever been so upfront about looking at me in a provocative way. At least that I wanted to look at me that way. He placed a hand on my hip and leaned in so I could hear him better. Only he talked even softer.“

    That Aussie has no discretion and was hitting everything with 2 legs and would still be objectifying / demeaning professional women while they’re at work if he hadn’t gotten so fat.

    • Frippery says:

      Jennifer Connelly and Russell Crowe didn’t date. Are you thinking of Paul Bettany maybe?

      Crowe would have been married during the period where Mystery Man and Simpson were seeing each other. So, he doesn’t fit anyway.

    • Becks1 says:

      He didn’t win for A Beautiful Mind but did win for Gladiator (I think he won the award in 2001 but the movie came out in 2000.)

      He was certainly a big movie star at that point, but is he someone Jessica would have grown up knowing? I don’t think I ever heard of him really before Gladiator.

    • Alexandria says:

      She grew up thinking he was hot. It sounds more like Tom Cruise. RC wasn’t a mega star in the late 90s. I’m Jessica’s age.

  23. Julia K says:

    Whoever it was, she can’t say because of the fear of reprisal. That leaves Tom Cruise and Scientology?

  24. Britney says:

    My first instinct was Leonardo DiCaprio because of how secretive Jess is being in her story. Leo doesn’t like anyone to kiss & tell, but this isn’t Leo’s style – he lets the girls come to him.

    I’m definitely thinking Marky Mark who was wearing jeans, combat boots & a bob marley t-shirt to the 2001 VMA’s. This is totally his vibe – friends with the security guard and the kinda guy who would look a pretty girl up and down every chance he gets. Fear, Boogie Nights, The Perfect Storm, Planet of the Apes & Rockstar all had come out prior to the event. He is totally Jessica’s type – there’s a lot of Marky Mark in young Nick Lachey. Mark also walked the red carpet of the 2001 VMA’s shortly after Jess did if you rewatch the live feed. Remember, he was dating his now wife but they didn’t get married until 2009.

    • AmelieOriginal says:

      I didn’t even think of Leo! He would have been super popular with Titanic coming out in 1998 but he wasn’t exactly a massive movie star in the 90s? He had done some things before Titanic but Titanic is what put him on the map. I know everyone seems to think it’s Mark Walberg but it makes more sense for it to be somebody like Tom Cruise? He had filed from divorce from Nicole Kidman earlier that year in 2001 and he famously dated Penelope Cruz after but Jessica could have been between Nicole and Penelope. Penelope and Tom broke up in 2004 and then Tom and Katie came out as a couple in April 2005. So I dunno, the timing could work?

      I don’t think it was Brad Pitt. He and Aniston announced their divorce in January 2005 and there were already rumors going around it was because of an affair (they definitely had an emotional affair, even if it wasn’t physical) with Angelina Jolie. The famous paparazzi pics of Brad, Angelina, and Maddox on the beach in Kenya came out in April 2005. So he was too busy dealing with that whole triangle, not sure how he’d been able to fit Jessica in amongst all that lol.

      I just can’t see it being Mark Walberg, he doesn’t have the charisma or the looks fitting Jessica’s description. Red carpets don’t part when he’s on the red carpet. I don’t think he’s even that good looking and I checked pics from 2001 to check.

      Also the VMAs are a very casual environment, tons of people show up wearing jeans and a shirt. The Oscars it ain’t! My aunt worked at MTV and often attended as an employee, I remember it well.

      • Becks1 says:

        I remember going to see Titanic in theaters either the weekend it opened or a week after and EVERYONE in the theater screamed in excitement in the opening few scenes, when you just sort of see Leo’s hands and hair over his eyes as he’s sketching Kate Winslet in the flashback. We were THERE for Leo. So I’m not sure when it exactly it happened, but we (teenage girls) went to Titanic in large part to see Leo, so he was already considered a heartthrob.

      • Britney says:

        It definitely positively absolutely was NOT Tom Cruise. All of tom’s +1’s were contractual obligations vetted by the Church of Scientology. This was well documented at the time. Tom has no time for real dating, and a pop star never would’ve been on the radar – Tom only dated actresses. Katie Holmes auditioned to be his girlfriend along with a host of others (Scarlett Johansson, Lindsay Lohan, Kate Bosworth, Jessica Alba, etc.).

        Mark Wahlberg was the only one wearing a T-Shirt and jeans at the VMA’s who would be that forward. Scroll through the photos from the event. Like I said before, Nick Lachey at this time had a LOT of Marky Mark going on with his personality and it totally fits Jess’s type during her walk-all-over-me phase (Jansen Ackles, Nick Lachey, etc.)

  25. FHMom says:

    I looked through so many photos. The only actors wearing jeans and a Tshirt were Will Smith and Mark Wahlberg. Smith brought his son, so I’m going with Wahlberg.

  26. Miss Melissa says:

    George Clooney.

    Clooney became a massive sex symbol in the early/mid 1990s with ER on television. Once he eventually started branching into movies everyone wanted him. He famously had a series of girlfriends one right after the other and never married until recent history.

    Oceans 11 was released in 2001 and was a massive hit. He had won acclaim for The Perfect Storm the year before and was one of the biggest movie stars around and already “Sexiest Man Alive” in 1997.

    • The Old Chick says:

      He’s my guess. Plus he does the smoulder thing and could reduce her to mush.

      • Brassy Rebel says:

        Clooney is the only one who fits the description and the timeline. He was a “massive” tv star before he was a massive film star. Anyone remember ER? He starred on that from the midnineties to 1999 then moved seamlessly to the movies. Before ER, he was a teen heartthrob on a couple of sitcoms. And by 2001, he could part a red carpet and probably the Red Sea. He fits. Cruise doesn’t smolder.

    • Yep says:

      LOL, except George prefers men though loves smart women. She’s not and never was his type. And George would be gentlemanly and fatherly with a woman, not sleazy and expertly rolling out a well-trodded seduction routine like this.

      • The Old Chick says:

        The George perfers men gossip seemed to have gone away the last few years. And it wasn’t widely mentioned before. I think these days it’s no big deal if he’s bi or whatever.

  27. HeyKay says:

    Oh, no Marky Mark, please. I can’t stand him.
    I hope it was Tom Cruise. Yes, I hate MW so much I’d prefer it was Tom Cruise. lol

    I guessed Colin Farrell right away just because Colin was gorgeous and a known charmer/ladies man. I can see Colin moving right in on JS with his lovely self, they would’ve made a beautiful couple.
    Liev S. or Russell Crowe, neither of them are handsome enough to qualify, IMO.
    Anyhow..this was some fun gossipy guessing. Thanks JC. 👍

  28. Tchotchke says:

    It’s Mark Wahlberg. He was a sex symbol when she was growing up in the 90s from the Calvin Klein ads & his short-lived music career. Wahlberg presented an award at the 2001 VMAs, and had started dating Rhea Durham around that time (Jessica later mentions seeing photos of him kissing the girlfriend he swore was not in the picture anymore.) Mark and Rhea would be off and on for eight years before getting married. Mark was a pretty notorious womanizer during those years.

    Other clues: he knows her trainer (Wahlberg is a known gym rat, who has done massive action films, requiring him to work with a plethora of entertainment industry trainers.) He was arguably at the height of his career around that point. He had done Planet of the Apes, the Perfect Storm, and Boogie Nights. He was being taken seriously as both a bankable action star and an actor who could do arty dramas.

    • Britney says:

      THIS! You are 1,000% correct with the trainer connection. I can’t with any other suggestions. This Blind Item has been SOLVED! MARKY MARK!!!!!!!!!!!!!!

      • Tchotchke says:

        She later mentions that he invited her to a set where even the most casual movie fan would know the director. He was in “The Departed,” which was a Scorsese film and fits squarely in the timeframe. (Jessica got divorced in 2006, which is when Wahlberg was making that film.)

        Add to that the fact that Marky Mark was wearing a t-shirt at the VMAs, was known to f*ck around on Rhea in the early years, and despite being a practicing Catholic, had a child out of wedlock (I’m sure his spiritual advisor helped him do mental gymnastics to justify that one), and yeah, it’s Mark. Also, let’s be real: Jessica has a type. She like built, All-American-looking guys. Relatively clean-cut looking, short hair, etc. This is so, so thinly-veiled.

    • Ashley says:

      I also think it was Mark Wahlberg in 2001 he was at the VMAs. He had a huge movie Rockstar out starring him and Jennifer Aniston and I definitely think the connection with the bodyguard and him were both gym rats.

  29. Stef says:

    Can’t be Liev, he’s not really known as a huge movie star, IMO.

    My gut says Marky Mark! He was a well known player and über douche back in the day (his history of violence is wild, and scary). Remember how he was THE hot guy with the CK underwear ads? Let’s not forget his hot, shirtless, Funky Bunch days. Plus, he became a huge movie star when Fear (with Reece Witherspoon) came out in the 90’s.

    Jessica and I are almost the same age and Marky Mark makes the most sense to me. I totally would have hooked up with him too back then if I’d had the chance. Today? Barf city. He’s gross!

    If you haven’t read Open Book, and you like memoirs, it’s great!

  30. Thelma says:

    Can I just say that she writes well and is funny as hell. I laughed out loud a couple of times reading this excerpt!

    • Yep says:

      Haha, her ghostwriter writes well, you mean! She probably recorded some videos for the GW to start on the draft.

      • Thelma says:

        Yes ,,but ghostwriters work with different clients and get different outcomes so I still think she’s probably pretty funny. #chickenofthesea

  31. Matilda says:

    I’m going with Matthew McConaghey.

  32. TheVolvesSeidr says:

    There is an interesting blurb today on Jezebel & their guess is also Mark Walhberg. In her short story, Jessica says about the mystery man that he would tell her how much he wanted to have sex with her but that it made him feel *sinful*. She also said they were both religious but diff faiths (she baptist marky mark catholic)… It’s Marky mark. He was hot when he was a boy band guy.

  33. Jackson says:

    Hmm. Was Johnny Depp at that show?? Clooney?? I don’t see him being that guy, tho.
    I’m thinking MW.

  34. Marisa says:

    This reads Mark Wahlberg to me. I have to say I have a soft spot for him. I used to work for a Boston area nonprofit that helps teens with emotional health issues. And he was filming nearby and we called the set and asked if he’d visit. Legit within hours he just showed up (with a large entourage, natch). He just hung out with the kids and the staff playing basketball and was super approachable and low key. It was fascinating to see how people LOST THEIR MINDS when they saw him. Must be so weird to be a huge celebrity.

    • Lucas Pinheiro says:

      I bet on Mark too. I can see Mark acting that way. I don’t think Tim Robbins would do that. He looked kind of out of place and appearing in photos with a member of O-Town, winner of the “Making the Band”.

  35. Lauren says:

    One thing that sticks out to me is she said he had a different faith than her and a spiritual advisor. If I recall correctly she is Christian. So who of the actors would qualify from 2001… I could see Mark Whalberg or Liev Schrieber… think about someone with the power to make her feel this way and also KNOW he has that power. I didn’t think of Mark but after reading the comments I am open to him being the guy. I also wondered if it could be a Scientologist…

  36. Pdiddy says:

    MW is not from the south. He is from Boston.

    • Becks1 says:

      Does she say he’s from the South? Because if so that absolutely eliminates Wahlberg, and Affleck and Damon as well.

  37. Smalltowngirl says:

    It was Romeo and Juliet that made Leo swoon worthy, Titanic just solidified it. He was also on a season of Growing Pains. Jessica is a couple year older than me and Leo was THE teenage crush of almost everyone I knew.

  38. June says:

    Sad that there are SO MANY to consider as viable options. Says alot about Hollyweird men. My vote is Pitt simply because he’s a major douche.

    • Saba says:

      – He was a MEGA star.
      – A Hollywood after-party room parted for him.
      – He was the definition of swoon.
      – He was her teenage fantasy and older than her.
      – He had a girlfriend but eventually split from her.
      – He’s still a movie star and a name even the most casual moviegoer would recognise.

      How could this be anyone other than Leo? Their interaction screams Leo!

      Also worth noting:

      In early 2007, Jess was seen following Leo around a club. She was newly single from John Mayer, and Leo was newly single from Bar Rafaeli (tho they got back together and eventually split).

      My guess is now that Leo was single, she was ok with the ethics of the affair. But Leo has an ego and holds a grudge so being the mature adult we know he is, he leaked that she was ‘stalking’ him and he wasn’t interested.

      Leo also has a thing for not publicly dating women who have famously dated anyone else. He likes them young and fresh. He doesn’t do leftovers. Gross but true.

      • Lux says:

        I would say 100% Leo except he never married. Leo was also in the Departed WITH MW, so the plot thickens…

      • Saba says:

        Oops made an error. It was the director of the film set Jess visited in 2006 who was well known, even to the most casual moviegoer.

        Scorsese fits the bill, except The Departed was released in 2006 and was in production in 2005.

  39. Queenie says:

    Somewhat unsubstantiated, petty speculation on a blind item is just what I needed today! Rough marriage therapy and lack of sleep puts today in the ‘not great’ category so genuinely, thank you 🙏

  40. LadyE says:

    All I know is that it definitely wasn’t Tim Robbins. He’s a good actor, but not at all swoon inducing. This would be the most misleading blind item ever for red-carpet parting, sexy megastar undressing Jessica Simpson with his eyes to turn out to be Tim Robbins lol

    • Celebs are Ghouls! says:

      Well, Tim Robbins would have been *my* swoon-worthy star, but I suspect Jessica & I have different tastes.

      Tho, how is Marky Mark considered a megastar now??

  41. Christine says:

    Jessica Simpson is writing about something that happened decades ago, and she’s Jessica Simpson. It would make my life if whoever this is (Mark W) just said something like, “It’s Jessica Simpson, of course I thought she was hot.”

    At the time, I was thinking, “why are all these hot guys into someone who doesn’t know what tuna is?”, but I get it now. She is still hot.

  42. Anna says:

    Wasn’t Justin Timberlake in the Mickey Mouse Club? Jessica could have grown up watching him there… haha

  43. Betty says:

    It was Mark Wahlberg

  44. vero says:

    I ´ d loooove to know who the Backstreet boy was …

  45. Brook says:

    It was Jared Leto