Keanu Reeves had ‘too much fun’ working with Winona Ryder again, omg

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Keanu Reeves and Winona Ryder are from the same “cool ‘90s” generation. They were HUGE deals in the 1990s, and since then, their paths diverged. Keanu’s star continued to grow and grow, and at this point, he picks and chooses his projects and passions because he has more money than God. Winona’s star faded in the 00s, but in the 2010s, she’s come back to a certain degree. It’s also worth mentioning that Winona and Keanu have been friends this whole time, ever since Dracula. They’ve worked together throughout the years, and they decided to do Destination Wedding together to show off their comedic chops once again. Here’s the trailer:

I don’t know… I think it looks really cute? I love that they both said yes to this script – Keanu doesn’t do enough comedic roles or romances these days, which is too bad because he’s great at them. And Winona needs more scripts like this too. At a premiere for his film Siberia last week, Keanu talked about Destination Wedding and how he and Winona have maintained their friendship:

Even decades into his career, Keanu Reeves doesn’t do half measures. “With each role that I play, I do give it my all,” he said at the New York premiere of his latest movie, Siberia, on Wednesday night at the Metrograph theater. “I love acting and making films as much as I did when I first started, and that was a long time ago. I just love being a storyteller. . . . There’s nothing else I’d rather do. I’ve had the chance to play really cool characters in some cool films; I just feel lucky and grateful.”

…His other movie, Destination Wedding, marks his first romantic-comedy in 15 years—since 2003’s Something’s Gotta Give with Diane Keaton. The new rom-com reunites Reeves with his 1992 Bram Stoker’s Dracula co-star Winona Ryder; the two play unhappy and gloomy guests attending a wedding in California wine country who develop an unlikely romance. The pairing of Reeves and Ryder is already generating buzz among Generation-X fans, who are clamoring to see the 90s idols together again on August 24.

“I had the best time working with Winona again. She’s such a great actress. We had fun together making Destination Wedding—too much fun,” said Reeves. “We play characters that are opposites of the same coin. I’m more of a pessimist, and she’s more of an optimist, which causes lots of fighting between the two of us. . . . I haven’t done a lot of romantic comedies, and I really loved the humor of the script and I loved all the dramatic experiences the characters go through.”

Reeves said he has remained in contact with Winona over the years through text messages. “It’s nice. She’s a friend,” he said. “I text Winona and write, ‘Hey, Winona, what are you doing?’ It’s awesome.”

[From Vanity Fair]

Forget Halle Berry, I would love to see Winona and Keanu end up together. COME ON. That’s like the Generation X fairy-tale: two ’90s icons who have been through some sh-t and been friends for decades, and then they get together in their 40s/50s? That would be amazing. It’s probably not happening, but MORE OF THIS.

Embed from Getty Images

Embed from Getty Images

Photos courtesy of Getty, promotional image from ‘Destination Wedding’.

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39 Responses to “Keanu Reeves had ‘too much fun’ working with Winona Ryder again, omg”

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  1. Frenchinhk says:

    Beautiful couple of vampires 🤩

    • Poer says:

      the last time it was halle, now wynona? people need to stop playig match maker to my keanu 🙁

  2. babypeanut says:

    She really looks like Lara Flynn Boyle, pre-face ruination, in that still of the trailer.

  3. SympathyRage says:

    He is one of the sweetest humam beings alive. He is up there with Bob Ross and Mr. Rogers and Julia Child. What a sweet, sweet man.

  4. Shannon says:

    OMG I *have* to see this movie! I love them!

  5. FhMom says:

    This makes my heart happy. I would love to see them together although that’s reading a lot into this.

  6. AnotherDirtyMartini says:

    That would be cute. Count me in as Keanona shipper.

  7. Morrissey says:

    Gather up the girlfriends for margaritas (smuggled in) and popcorn. I’m all in. My heart needed this.

  8. WTW says:

    Winona’s cool, but I don’t think she’s any more stable than Halle Berry, so I disagree that a Noni/Keke coupling would be any better than a Halle/Keke coupling. You say her star faded in the 00s, but that was largely due to her shoplifting scandal. It didn’t happen randomly. I thought she was unfairly ostracized then, but she was found to have lots of prescription drugs at the time and overall seemed like a very troubled person. I’m sure she’s in a healthier place now but doubt all of her demons have vanished. Also, you forgot that Keanu and Winona also starred in A Scanner Darkly together, and that came out in 2006. I do think it says something about Keanu that he’s starred in movies with the same leading lady — Winona, Charlize, Sandra, Rachel Weisz — at least two or three times. These women must think he’s a nice guy to keep working with him.

    • Lani says:

      I totally agree wow but also I like the keke/halle there pairing is what a called hot and sexy while keke/Winona pairing is cute.I disagree with you Kaiser that Winona is better than Halle I love both but they unstable and cray

  9. ChillyWilly says:

    Lmao @ “Hey Winona! What are you doing?” He’s so sweet and cute 😍! They look purty together.

    • zinjojo says:

      Haha, Keanu’s texts are like my mom texts to my college student kid! I love them together and really hope the movie makes the most of their talent and is a good romcom. We all NEED this right now — something good and fun and light.

  10. harla says:

    From the trailer it looks and sounds like John Wick is going to a destination wedding!! I think that would be even funnier!!

  11. Seraphina says:

    Looking at the last photo of Keanu, I forgot what a fine looking man he was back then. Damn. You go Winona.

    • Miss M says:

      I eent to check the photo again and then I realized Harvey W is behind Winona. Ewww
      But yeah, Keanu was really handsome.

      • ravynrobyn says:

        WAS really handsome? He never EVER stopped being handsome! Aging like a spectacular fine wine, yummmmm.

      • NotSoSocialButterfly says:


        I adore him and still think he is handsome, but there’s too much botox in his forehead. He also could use some Rembrandt toothpaste.

        Cut the cigs, Keanu.

      • Nova says:

        He is still hotter than many younger heartthrobes.

      • ravynrobyn says:

        @ NotSoSocialButterfly-I usually don’t notice botox, so I’ll have to inspect some Keanu pix 😉

        ITA agree w/ the Rembrandt toothpaste too.

        I dunno, maybe it’s my age? When I look at him I still see Johnny Utah and the pain in his eyes. Like catnip, I tell you 🤣

        Nice chatting with u!

    • isabelle says:

      Think he is even hotter now, I like the beard and the tiny wrinkles of time.

  12. supersoft says:

    The trailer looks really good, i need to see it.

  13. D says:

    SMILING KEANU I’m dying over here and JUST LAST NIGHT was saying to my son I need some old school 90s romcom never could I imagine THIS GIFT of also Winona IM YELLING YALL LOLOLOL

  14. Yes Doubtful says:

    I’m not a Reeves fan because I think he’s a terrible actor (the surfer voice!), but I loved loved loved Ryder in the 90’s! She has so many great movies! I’m looking forward to this one!

    • Jerusha says:

      He’s not DDL, agreed, but I can’t imagine anyone else as Ted or Neo, Johnny Utah, Jack Traven, Scott Favor, John Wick. And catch him in The Gift, in which he plays a Southern redneck. He’s excellent and holds his own opposite Cate B. and Hillary S. Some of his best work has been with awards winners like Sandra, Cate, Charlize, Rachel, Pacino, Hackman, when he doesn’t have to carry the whole movie.

  15. Neelyo says:

    I always thought Ryder was overrated as an actor.

  16. Miss M says:

    I really want to see it. They look so great together. But then again, who doesn’t look good with Keanu by her side?! 😉

  17. paddingtonjr says:

    I am so there for this! I’ll have to see it with my girlfriends in a drafthouse cinema because much wine-drinking and squealing are going to happen! I’m not really a fan of cute rom-coms, but this looks like a grown-up version with two people who went through the “strike while the iron is hot, be in everything, suffer from exhaustion” period and now can just enjoy their successes. I love how Keanu always seems to be appreciative and grateful for his career and that he not only works with the same actresses more than once but that he seems to make life-long friendships with them.

  18. cannibell says:

    I just watched the trailer and it looks like enormous fun. {grabs popcorn…..waits….}

  19. SJhere says:

    Take my money! I love Keanu! Oh, not like some people who “claim” to love him.
    I LOVE him. I have paid good American cash to go to the movie theater and see a movie just because Keanu is in it. Keanu forever!
    p.s. If Speed had been 15 minutes shorter it would have been a better movie. Generation Um, To the Bone and The Bad Batch were all a waste of everyone’s time, how Keanu signed on for these projects, I don’t know. Watch for Keanu as a burglar/hitman in I Love You to Death, very funny in that. And, yes he was very good in The Gift. (Also, stunning looking. He was in his gorgeous long hair prime in this.)

  20. raincoaster says:

    This actually looks charming, and I’m going to see it for sure. I like how sort of Bill Paxton-ish Keanu’s character is. Dry and low-key, with a stealth bitchiness.

  21. Karen2 says:

    ….I understand why you say he has more money than God but it could actually all be gone …like Lisa Marie…like Johny…like MJ….which would explain all the crap movies hes been in recently…

  22. Madpoe says:

    I’m excited to see this! I hate Rom-Coms but love Keanu and Winona.

  23. holly hobby says:

    Ah Keanu. What a fine man. I would love to watch a smiling Keanu movie!