Kiefer Sutherland showed up on The Late Show last night… wearing a dress. Yeah. I didn’t see the huge deal about it, because let’s face it, Kiefer is kind of crazy (but still kind of hot), and wearing a dress on Letterman isn’t even in the top ten (get it?) dumb things Kiefer has ever done. Anyway, Kiefer wore a dress because he lost a bet. Because I hear that gambling is a really good way to kick alcoholism, right, Kiefer?

Gamblers beware: losing a bet can make you look foolish. Just ask Kiefer Sutherland.

The hard-core action star of Fox’s “24″ sat with David Letterman on the “Late Show” Wednesday night dressed in a hideous peacock-inspired dress after losing a bet to a buddy.

“I lost a bet over the weekend,” he told Letterman, the embarrassment displayed clearly on his face. “I was so sure New England was going to win, that I told a guy who used to be my friend that if New England lost, I would wear a dress on ‘Letterman’.”

The Patriots lost to the Baltimore Ravens on Sunday, 33-14.

“And so, here I am,” he noted, sheepishly.

Sutherland, who gets credit for going through with the bet, accessorized the dress with combat boots and a long-sleeved white t-shirt.

Letterman offered the 43-year-old actor $1,000 to wear the outfit on the subway.

“Riding the subway would be easier than what I’m going through right now.”

Although the conversation eventually turned to Sutherland’s return as Jack Bauer on “24″ this Sunday, the dress made serious conversation impossible.

“This may be the most humiliating moment of my life,” Sutherland said with a smile. “And I’ve had quite a few to choose from.”

At the end of his segment, Sutherland ran off stage as band leader Paul Shaffer played him out with Aerosmith’s “Dude looks like a lady.”

[From The NYDN]

I could be going too hard on Kiefer, but I lecture because I love. I love him and his father, I think they’re both amazing actors, and it pains me a little that Kiefer has such a screwed up personal life. By the way, if you think the dress is bad (which it is), check out what Kiefer wore to the studio - a swear, this is a denim suit. I spent too much time looking at the cut of that jacket, and that bitch is tailored like a suit jacket. Kiefer actually picked that out for himself, you know he did. That boy isn’t right in the head.

Kiefer Sutherland outside of the Ed Sullivan Theatre on January 13, 2010. Credit: WENN.

It’s generally acknowledged that Kiefer Sutherland can party hard. He’s got several stints in rehab under his belt to prove it. There’s this story going around from TMZ about how Kiefer blew $700 on his bar tab from 7 in the morning until 1 o’clock in the afternoon last week. Yes, your jaw is supposed to hit the floor. But despite the way their intro paragraph makes it sound, they acknowledge he was actually just being a good guy.

Kiefer stopped in with about 30 members of the crew from 24 – after what must have been a very early shoot. He paid for everyone’s drinks, which came out to $500 (or about $16.66 per person on average); and he left a $200 tip.

Kiefer Sutherland racked up the following $700 bar tab between 7am and 1pm. Yes, those times are correct.

We’ve learned the “24″ star and members of the show’s crew popped into The Spot in San Pedro, California last week after wrapping up a shoot nearby — and they were ready to get their drink on.

According to an employee at the bar, Kiefer was throwing back scotch & Cokes and bought drinks for everybody in the joint — roughly 30 people. The total damage: $500. No food … all booze.

The drinks may have been stiff, but Kiefer wasn’t — we’re told he tipped $200.

FYI: We’re told Sutherland — who has a few DUIs under his belt — was responsible this time and used a designated driver when he left the bar.

[From TMZ]

It’d be extra nice if the story were about how Kiefer nursed some ginger ales and made sure everyone had a good time. While it doesn’t seem like he’s taking his sobriety seriously, and least he’s taking his responsibility to the law more seriously. And I guess that’s something. If I were on the crew, I would have been sort of nervous about the whole thing. It just seems like he’s asking for trouble and tabloid headlines. Everything considered, it sounds like Sutherland was gracious all the way around – TMZ has some funny photos taken at the bar.

Here’s Kiefer dining at the Spotted Pig in New York City on October 1st. Images thanks to INF Photo.

Kiefer Sutherland is going to surrender himself to New York authorities a few weeks from now, all stemming from “a minor assault charge” lodged against him for headbutting Proenza Schouler designer Jack McCollough. Even though I want to think well of Kiefer for sort-of defending the honor of a lady (Brooke Shields), he must have some serious issues. Brooke even sides with McCollough, because she had her representatives tell TMZ that she was jostled, but nothing happened. Ah, it seems the fair damsel in distress didn’t really mind when her martini was shaken.

Kiefer’s friends are still trying to make excuses, though. An unnamed friend tells the New York Daily News that though Kiefer feels strongly that he was “provoked”, Kiefer is totally sorry, and thinks the incident was “regrettable”:

Kiefer Sutherland will surrender to prosecutors in several weeks and face only a minor assault charge for headbutting a fashion designer at a party, a law enforcement source told the Daily News.

Sutherland, who spent Wednesday holed up in his girlfriend’s Manhattan apartment, will face only a third-degree assault charge for the bizarre assault on designer Jack McCollough, sources said.

And the actor will simply be issued a desk appearance ticket for the misdemeanor - meaning he won’t be jailed and will be free to travel before his arraignment date.

A friend told the News that Sutherland - who seemed to be channelling his “24” alter ego Jack Bauer when he slammed his head into McCollough’s at a Soho nightspot - felt bad about the strange display.

“Kiefer is sorry it happened. Absolutely. It’s terribly regrettable,” said the friend.

Still, the friend insisted Sutherland lashed out inside SubMercer because McCollough, a designer for Proenza Schouler, bumped into actress Brooke Shields.

“Kiefer was provoked. The gentleman bumped into Brooke Shields and didn’t apologize,” the friend said.

Sutherland’s attorneys are expected to contact McCollough’s lawyers and hammer out a cash settlement.

Sporting a fresh cut across the bridge of his nose and shielding his eyes with Oakley sunglasses, McCollough told the Daily News this morning outside his West Village apartment that he’s “doing fine.”

McCollough’s representatives are resolute that the head smacking at an after-party for the Metropolitan Museum of Art’s annual Costume Institute gala was unprompted, telling People, “Anyone who knows Jack McCollough knows that he would not hurt a fly.”

“All we can say at this point is that he was the victim of a vicious, violent, unprovoked assault and that the matter is in the hands of the authorities.”

Shields’ is apparently siding with McCollough, with her reps telling TMZ that she was jostled but “nothing happened to her.”

When Sutherland is formally charged in New York, it could violate the conditions of his probation for a 2007 drunken driving charge in Los Angeles - and potentially send him back to jail.

The actor was put on five years probation after serving 48 days in jail for driving under the influence in 2007. He was on probation for a 2004 drunken driving charge at the time.

“There is an ongoing investigation, and we’ll wait until that is concluded,” said Frank Mateljan, spokesman for the Los Angeles city attorney’s office.

“We would need to see the specific facts of what happened before we make a determination as to whether or not probation has been violated.”

[From The New York Daily News]

McCollough’s people are talking directly to People Magazine, and they sound pissed. In addition to the “he would not hurt a fly” argument (which I believe, the guy looks like a stiff wind would blow him over), Jack’s reps say: “All we can say at this point is that he was the victim of a vicious, violent, unprovoked assault and that the matter is in the hands of the authorities.”

There’s even consternation about exactly how the headbutting went down. One of McCollough’s people also tells People Magazine: “Jack walked into the party and tried to order a drink, and then the next thing he knew, he got headbutted for no identifiable reason… Jack did nothing other than walk into a party. He did not bump into Brooke. It’s just puzzling.” Ah, yes. But Kiefer sensed that there was a damsel in distress, you see. Thus, headbutting.

Keifer Sutherland got into a fight at an after party for the Metropolitan Museum of Art’s star-studded Costume Institute Gala. The 42 year-old star of “24″ headbutted a designer, breaking the guy’s nose and sending him to the hospital. According to different accounts, designer Jack McCollough either knocked over or bumped into Brooke Shields and Sutherland rushed to her defense, telling McCollough to apologize. McCollough refused and pushed Sutherland instead, which prompted Sutherland to headbutt him in the face. Shields rep says that there was no incident with his client which would have made Sutherland come to her defense:

Women’s wear designer Jack McCollough found that out the hard way when he cut between Jack’s alter-ego, Kiefer Sutherland, and Brooke Shields as they were schmoozing at a SoHo nightspot and got a whopping head-butt from the “24″ star, police said.

Some witnesses said McCollough, co-founder of the white-hot Proenza Schouler label, suffered a broken nose in the bell-ringing Tuesday morning at SubMercer, but he told cops all he got was a small cut on his schnoz.
Investigators from the 1st Precinct have the misdemeanor case now and are reaching out to Sutherland to get his side of the story.

Some witnesses said Sutherland went into action hero mode after McCollough bumped into Shields as she and Sutherland talked at the bar about 2 a.m.

Sutherland took offense and demanded the designer apologize to Shields.

But the two men got into a heated argument that ended with Sutherland head-butting McCollough, a police source said.

Shields, who may be talking to cops today, apparently is taking McCollough’s side.

Her reps say the designer did nothing to deserve the head-butt and although Shields did get jostled, possibly off her feet, “nothing happened to her.”

McCollough told investigators Sutherland “was drunk and obnoxious and wouldn’t back down or be logical.”
He said Sutherland “pulled this stupid wrestling move like a teenager,” then slammed McCollough in the face.
A police source quoted McCollough as saying the dustup “wasn’t even over anything . . . he was just roiling drunk and looking for something to smack. It didn’t matter what.”

[From The Ny Daily News]

Sutherland spent the 2007-2008 holiday season in Glendale City Jail, where he served a full 49 day sentence for a September, 2007 DUI, his second in under three years. With his second DUI he violated probation for his previous DUI from 2004. The judge presiding over his case was Judge Michael Sauer, who put Paris Hilton in jail for a full 45 days for just driving on a suspended license.

With this latest fight, Sutherland has violated probation for his last DUI, although it’s unknown if he’ll have to face charges back in California. The guy went to jail for over a month and a half and was also assigned six months of weekly therapy, five years probation, and an 18-month alcohol education program. Considering that he only got out of jail in January, 2008, he’s probably still in alcohol education classes. He’s been seen getting wasted all over NY and this latest incident just makes the fact that he’s fallen off the wagon all the more public.

Sutherland is one of the highest paid stars on television and according to AOL Television makes $13 million a year.

Kiefer Sutherland is shown outside the Late Show on 4/27/09. Credit: WENN.com

24 is returning early to the Fox network, having been previously delayed by the writer’s strike and Kiefer Sutherland’s DUI jail time. The series was originally not going to make it to television until early 2009.

The new series, which was originally due to air Stateside in January 2008, will now not go out until January 2009.

To help fans make the transition over the long break, a made-for-TV prequel is planned for the autumn. The two-hour special will be set in Africa a year after the events portrayed in day six.

“(Jack’s) a soul in turmoil and has been moving from place to place trying to find somewhere he can be at peace,” explains a source. “But he winds up in Africa in the middle of a coup.”

Hello Magazine

The programme will lay the groundwork for next season’s action which begins and ends at 8am and plays out against a Washington backdrop.

Is Fox bringing back 24 for a special event to test how audiences feel about Jack Bauer now that Kiefer has done some jail time? I’m not sure how much Kiefer’s reputation has been sullied by the drink driving arrest and prison sentence. While it was hardly a first offense, in fact I think you might describe his drinking as a ‘problem’, people didn’t seem to react the same way they did when Paris, Nicole and Lindsay were arrested. Maybe there’s a different standard for women when it comes to a DUI arrest.

It’s possible the network is also hesitant to commit to a full length series because of the anticipated actors strike. I hope the strike doesn’t go on for too long, if it does go ahead. Another season of tv like this one and I’ll turn my television into a fish tank.

Just for a laugh, here’s Kiefer getting arrested for the new series. It’s like a reenactment for those of us that missed the real life drama. Will this be shown on 24 or America’s Most Wanted?

Picture note by Celebitchy: Kiefer Sutherland is shown on the set of “24″ on 5/11/08, thanks to Splash News.

Donald and Kiefer Sutherland at the 2006 Emmys
Since his release from jail for DUI earlier this month, “24” star Kiefer Sutherland appears to be a model citizen—keeping a low profile, staying out of trouble and even spending some quality time with his father, actor Donald Sutherland, currently the star of the ABC hit “Dirty Sexy Money.”

Kiefer, who has been recorded in various stages of drunken undress and infamously attacking an innocent Christmas tree in a hotel lobby, has had an up-and-down relationship with his famous dad for years. Reportedly, Donald pulled some strings behind the scenes to get Kiefer’s acting career started back in the ’80s, and Kiefer has spent years trying to distance himself and prove his talent away from his father’s influence.

In a recent statement, Donald, who struggled with his own substance abuse problems in the ’70s, commended his son for owning up to his mistakes and accepting his punishment accordingly:

DONALD SUTHERLAND has applauded his son KIEFER’s “perfect” behaviour in the aftermath of his arrest for drink (sic)-driving in September (07). 24 star Kiefer will spend Christmas behind bars after a Los Angeles judge sentenced him to 48 days in jail for driving under the influence.

But Donald insists his son conducted himself in an “honourable” manner and that other people, who he refuses to name, behaved in a disrespectful way at the time of the incident.

Sutherland Sr says, “You don’t want to get me going on this. All I can tell you is that he (Kiefer) is the most honourable, responsible, decent man I know, and I love him with a passion.

“(Kiefer) behaved in a way that was so pure and so perfect and so respectful.
There are other elements in our community that were less so, but he was perfect.”

[From PR Inside]

Hmmm. Could that be a dig at the Lohans and Hiltons of the world?

Kiefer and Donald were photographed, smiling and walking together, outside Mr Chow restaurant not long after his release from jail. These two are rarely photographed together—and Kiefer is more rarely photographed smiling. Hopefully, he can learn something from his time in jail and get help for his addiction. It seems like his dad is a great support system these days.

Picture note by Celebitchy: Kiefer and Donald Sutherland are shown in an image from the 2006 Emmys. Page Six has the photos of father and son hugging recently before having dinner.

Though I’ve complained a lot recently about the easy sentences celebrity criminals have been given lately, I’m pleased to report that Kiefer Sutherland will be let out of jail on Monday– after serving his entire sentence. He asked the judge to serve his jail time in Glendale’s city jail to avoid having to go to the massively overcrowded downtown Los Angeles County jail. But he couldn’t get any time off for good behavior or early release due to overcrowding at Glendale. Which makes me think L.A. County must be really miserable if someone would make that trade. By all accounts, Sutherland was a model inmate. Something tells me considering his long history of drinking issues; it’s good that he’s learned how to do his time.

Kiefer Sutherland, who plays the hard-as-nails agent of TV’s “24,” was a softy during his 48 days in jail on a drunken-driving charge. Sutherland, scheduled to be released Monday, has spent his sentence cleaning sheets, pillowcases and blankets on laundry duty, police Officer John Balian said Friday.

“He was very humble, never complained,” Balian said. “He didn’t give us any problems at all.” Sutherland, 41, pleaded no contest in October to driving with a blood-alcohol level above the legal limit of 0.08 percent. He was sentenced to 30 days, as well as 18 days for violating probation stemming from a 2004 drunken-driving arrest.

After entering his plea last fall, Sutherland issued a statement saying he was “very disappointed in myself for the poor judgment I exhibited recently, and I’m deeply sorry for the disappointment and distress this has caused my family, friends and co-workers.”

[From the Huffington Post]

I think the long-term(ish) incarcerations of Kiefer Sutherland and Paris Hilton have almost renewed my faith in the celebrity justice system. Note that I didn’t just say justice system, since celebs seem to have their own separate legal system. Nicole Richie’s and Lindsay Lohan’s 80-some minutes in jail were a pretty big letdown, but hopefully the tides are slowly starting to turn, and we can expect our favorite celebrity offenders to do some quality time in the near future. I’d love to say we can expect our favorite celebrities to stop committing crimes and shape up, but that trend unfortunately seems to be moving in the other direction. Next time around, we’ll hear about Lindsay Lohan on janitorial duty and Nicole Richie being traded for a pack of cigarettes. Few things make me happier.

Picture note by Jaybird: Here’s Kiefer Sutherland at the 2007 FOX Primetime Emmy After Party on September 16th . Images thanks to PR Photos.

Kiefer Sutherland won’t be getting any breaks on his prison time. Though it was originally thought that he wouldn’t actually serve many hours on his 48 day sentence for DUI and probation violation, it turns out that he will do every single day. It was believed Kiefer, 40, would get time off five days a week to go to work, and have to report to jail for the evenings and weekends. Yeah, doesn’t that sound nice. If everyone got that, I think 95% of the population would recklessly commit crimes. You get to go to work, save your cash, and flop down on a free (albeit concrete) bed with a complimentary dinner every night. Yeah it’s not plus, but think about it – every dollar you earn would be pure profit. Apparently realizing that getting to go to work on a catered television set with your own private trailer wasn’t much of a punishment, Judge Stuart M. Rice sentenced Sutherland to the full 49 days in the Glendale City Jail along with five years probation, and six months of weekly therapy, and the mandatory completion of an 18-month alcohol education program. Kiefer cannot earn time off for good behavior or work release.

“Mr. Sutherland is very polite and humble. He was very cooperative during the booking process,” said jail spokesman Officer John Balian. “He will be issued an orange jumpsuit, and will be housed alone in a cell, since he’ll be a long-term inmate.” Sutherland will be assigned to laundry and kitchen duty, serving breakfast, lunch and dinner to the other inmates. As an inmate worker, he’ll be allowed the roam the jail “about 75 percent of the time” – rather than be confined to his cell all day – though the only time he’ll be in contact with other inmates is when he’s serving food, said Balian.

Sutherland previously released a statement saying, “I’m very disappointed in myself for the poor judgment I exhibited recently, and I’m deeply sorry for the disappointment and distress this has caused my family, friends and co-workers on 24 and at 20th Century Fox. I appreciate the support and concern that has been extended to me these last weeks both personally and professionally.”

[From People]

Kiefer’s new residence won’t be nearly as nice as his plush mansion. His trailer, relatively Spartan when compared to his home, is absolutely luxurious compared to his cell, which measures 8 by 10 feet. It has a toilet, water fountain, and a sink. He’ll get two hot meals a day and one cold – generally a cereal breakfast. Like Paris Hilton and all the Hollywood socialites before him, he’ll get a simple diet of turkey and bologna sandwiches supplemented with the occasional macaroni, meatloaf, and chicken.

Kiefer seems to be a pretty hard-living kind of guy, so I’m reluctant to give him the old “Hopefully this will turn him around” treatment. But you never know. He’ll either realize nothing’s worth bologna, or start to get used to it.

Picture note by Celebitchy: Header image is Keifer’s booking photo, thanks to Splash News.

Kiefer Sutherland not only committed a second DUI in under five years, a crime that will get him a mandatory five days in jail under California law if he’s convicted, he violated his probation. And TMZ points out that the judge for the case for which he violated probation, a 2004 DUI, is none other than Judge Michael Sauer, the guy who put Paris Hilton in jail for 45 days for driving on a suspended license.

Sutherland has a long history of driving-related arrests, and the judge could that into account.

He was also busted in 1989 and 1993 for reckless driving. Both incidents had DUI charges, which were dismissed. His 1989 arrest also including charges for carrying a concealed, loaded firearm, but that didn’t stick either.

Now he’s still on probation for that 2004 DUI, and getting another DUI three years later isn’t going to bode well for him. What seems most damning for Sutherland is the fact that Judge Sauer could be presiding. He sent Paris Hilton away and then made sure she stayed in jail and didn’t get a medical pass from the warden. It’s unclear to me whether he will still have jurisdiction over Sutherland’s case, but he’ll be sure to get a lesson if that guy is in charge of sentencing.

Sutherland is due in court on October 16.

Kiefer Sutherland is shown in a tux at the FOX Primetime Emmy After Party on 9/16, and in a brown shirt at the FOX TCA All Star Party at the Pier on 7/32/07. Thanks to PRPhotos.

24 star Kiefer Sutherland has been videotaped, photographed and witnessed in various compromising drunken situations, including performing karate in a restaurant, attacking a Christmas tree, and subsequently passing out on the floor of a hotel lobby, and taking his pants off at a restaurant. He’s pretty straightforward about his issues, and calls the Christmas tree incident his most embarrassing moment.

Now Sutherland has been popped for DUI for a second time in five years. He was pulled over at 1:34 AM in Hollywood after making an illegal U-turn last night and blew over twice the .08 limit on the breathalyzer. He was booked at 4:09 AM and got out about an hour an a half later after meeting bail of $25k. He was said to be cooperative in jail. Sutherland is due to appear in court on October 16:

TMZ has learned that “24″ star Kiefer Sutherland was busted on suspicion of DUI in West Hollywood last night, after allegedly blowing more than twice the legal limit of .08. This is the actor’s second DUI in the past five years — he was arrested in 2004. By California law, if he’s convicted, he must serve a mandatory minimum of five days in jail.

Police sources tell TMZ 40-year-old Sutherland was pulled over around 1:35 AM PST on the corner of La Cienega and Beverly. Sutherland was at the FOX Fall Eco-Casino party at Area nightclub earlier that evening. The photo in this story was taken at the event.

Sutherland, who was stopped after making an illegal U-turn, was arrested for misdemeanor DUI and transported to the Hollywood Police station. He was booked at 4:09 AM and released at 5:42 AM on $25,000 bail.

We’re told Sutherland was “cooperative and mellow” while he was in custody.

According to the L.A. Sheriff’s Dept. website, the actor is 5′10″ and weighs 150 lbs.

Sutherland is scheduled to face a judge on October 16.

[From TMZ.com]

If Sutherland is convicted or pleads guilty he faces a mandatory minimum of five days in prison. It seems like he’ll be the next celebrity to go to rehab in the hope of avoiding a stricter penalty for DUI. He should stay the hell away from Cirque Lodge in Utah. Lohan already has her hands full there with Richie Sambora, and another celebrity will just add to her already heavy workload.

Seriously, he could have killed someone and should face the penalty for his actions. It’s one thing to engage in drunken hijinks harming flora, it’s another to put people’s lives at risk.

Thanks to CityRag for the header image.