The Gawker Wasted 20S

Click to viewIt's shaping up as a cruel summer for drunk, high or otherwise messed up celebrities trying to stay on the straight and narrow. Comedian Andy Dick was arrested this week for groping a 17-year-old's breasts while in possession of marijuana and Valium, in something of a reprise of his bust last year for doing blow in a nightclub. Actress and teen rehab veteran Drew Barrymore is now reported to have boozed her way to a breakup with actor Justin Long. Heather Locklear fled "depression and anxiety" rehab in Arizona after barely two weeks. Even a Rolling Stone, Ronnie Wood, surrendered himself to rehab again after leaving his wife for a 19-year-old cocktail waitress — and two bottles of vodka per day. Maybe all that summer daylight is pushing everyone over the edge! In any case, it's tough to keep track of who's where on the customary arc of high-profile substance abuse: embarrassment, criminality, rock-bottom desperation, rehabilitation and then either another trip around the circle or a break into the freedom of sobriety. That's why we've compiled a guide to once and future inebriated celebrities: 20 actors, singers, models and socialites who hog way more than their fair share of space in the gossip pages — and here on Gawker. We'll update and expand this list over time as a sort of encyclopedia of shame; your comments and tips are encouraged. (The arrows, by the way, indicate trends in drunkenness, so an upward arrow means getting drunker, downward means getting more sober.)

The Gawker Wasted 20S

Andy Dick, comedian

The Gawker Wasted 20

How drunk: Groping minors, getting arrested — classic Andy Dick, basically.

Latest: Nabbed by the police in Murrieta, California for drug use, posession of marijuana and Valium and for sexual assault after Dick grabbed a 17-year-old's breasts at 2am outside (sigh) "Buffalo Wild Wings Grill & Bar."

Outlook: Given his long and distinguished track record, a relapse is virtually guaranteed.

Low point: Beaten up at the Laugh Factory in Los Angeles in July 2007 by fellow comedian Jon Lovitz, who blamed him for the death of comedian Phil Hartman since Dick allegedly sold cocaine to Hartman's wife, a recovering addict, before she killed Hartman.

The Gawker Wasted 20Jessica Simpson, singer

The Gawker Wasted 20

How drunk: Drunk at lunch, but not drunk driving.

Latest: Perhaps distraught at pictures of ex-flame John Mayer with actress Jennifer Aniston, Simpson last week went on a four-hour margarita binge at LA's Mexicali Cocina Cantina that ended with her friend puking under the table and Simpson abandoning her car.

Outlook: Her clean track record offers hope this was an isolated boozing, but she needs to get over Mayer.

Low point: The restaurant thing. Simpson was once a goody two-shoes, having started singing in a Baptist church before transitioning to harmless teen pop. She remained a virgin prior to her first marriage.

The Gawker Wasted 20Amy Winehouse, singer

The Gawker Wasted 20

How drunk: Epically.

Latest: Thinks her home is inhabited by ghosts; caught smoking crack or something on video; punched, headbutted and stiffed three different people over the course of a single night; has a skin condition associated with crack addicts.

Outlook: Will probably deteriorate until she runs out of money or comes, somehow, closer to death. Rumors continue to circulate she'll seek treatment abroad, for example in Israel or South Africa. Whatever — these reports have been floated repeatedly in recent months and have yet to pan out.

Low point: Probably whatever is in the British tabloids on any given morning. Has had major issues at least since she's been famous. Her first U.S. hit was called "Rehab," after all.

The Gawker Wasted 20

Drew Barrymore, actress

The Gawker Wasted 20

How drunk: Engagement-breakingly, allegedly.

Latest: Dumped by actor Justin Long (whom she reportedly planned to marry) after he "got tired of having to help Drew to the car at the end of the night," according to the National Enquirer. After battling drugs and alcohol as a child star, Barrymore thought she had things under control.

Outlook: Decent: Continues to work, and normally tends to keep herself out of the tablouds.

Low point: Entering rehab at age 14, having already snorted cocaine.

The Gawker Wasted 20Mischa Barton, actress

The Gawker Wasted 20

How drunk: Problematically.

Latest: Pled no contest to drunk driving charges dating to December, got three years probation and mandatory alcohol-education classes.

Outlook: Decent. Has largely avoided the tabloids save for the December incident. Recently declined to join the case of Gossip Girl to work on another project, so apparently staying (soberly) busy.

Low point: Puked in the street last year while partying with celebrity friends Kirsten Dunst and Jamie-Lynn Sigler.

The Gawker Wasted 20Kirsten Dunst, actress

The Gawker Wasted 20

How drunk: Not? Rehabbed and hopefully not backsliding, despite that one rumor.

Latest: Dragged All Good Things co-star and rumored boyfriend Ryan Gosling to Alcoholics Anonymous meetings, a recovery no-no. Is fresh out of two-month rehab stint in April.

Outlook: Decent chance of a relapse. She's 26 with no kids or long term relationship, and with one hell of a track record.

Low point: When so many anonymous tipsters emailed us about her getting drunk around New York that we had to run a special report.

The Gawker Wasted 20Scott Weiland, singer

The Gawker Wasted 20

How drunk: Problematically.

Latest : The bipolar Stone Temple Pilots frontman served a 10-hour prison term earlier this month for a November drunk driving incident, his second in five years.

Outlook: Worrisome. With a wife of eight years and two children, hopefully the drunk driving incident was just a rocker's aberration, but it was his second in five years.

Low point: A two-month drug binge with Courtney Love in a hotel in 1998. Runners-up: Convicted of buying crack in 1995 and of driving drunk in 2003.

The Gawker Wasted 20Eva Mendes, actress

The Gawker Wasted 20

How drunk: Menacingly, but supposedly all better.

Latest: Checked herself into the Cirque Lodge rehab facility in Utah in January to "privately attend to some personal issues."

Outlook: Bad. Has taken a movie role playing a Spanish drug lord in Queen of the South. This could mean the rehab stint was just method acting; more likely the drug lord role will do to Mendes what Less Than Zero did to Robert Downey Jr.

Low point: The recent rehab. No history of erratic behavior, unless you count posing topless in Italian Vogue.

The Gawker Wasted 20Sean Young, actress

The Gawker Wasted 20

How drunk: Freshly rehabbed as of February.

Latest: Completed a sting in rehab earlier this year after being ejected from a Hollywood awards ceremony for bad behavior.

Outlook: Poor, due to a history of emotional volatility and bizarre behavior. According to Wikipedia, her role in Wall Street was reduced due to fights with Oliver Stone; she was sued by actor James Woods for harassment; she unsuccessfully tried to win a role on Batman Returns by confronting the director in a homemade Catwoman costume; she was fired from the movie Dick Tracy. Her last marriage ended in 2002.

Low point: Heckled director Julian Schnabel during his speech at the Director's Guild of America awards in January. Believed to be intoxicated, she was escorted out.

The Gawker Wasted 20Justin Chambers, actor and former model

The Gawker Wasted 20

How drunk: Not. Finally getting rested after a recent hospital stay.

Latest: Checked himself into UCLA Medical Center with what he said was a sleep disorder. But after his discharge, was spotted passing out and acting bizarrely at the Village Pub in Palm Springs.

Outlook: Good, if you make the difficult assumption he's telling the truth about his sleep disorder and that reports he was only drinking non-alcoholic beer at the pub are true.

Low point: The Village Pub incident.

The Gawker Wasted 20Miley Cyrus, singer and actress

The Gawker Wasted 20

How drunk: At 15, has possibly never been drunk. Then again, maybe there is something to these pictures of her stumbling out of a club in Hollywood.

Latest: Her scandalous, topless-except-for-a-sheet photo spread in Vanity Fair, obviously. Also, she keeps emailing underwear pictures to her boyfriend, which somehow end up online. None of which indicates she is on a path toward drinking or addiction, just that she is growing up and clearly ready to move beyond her goody-goody image on the TV show Hannah Montana.

Outlook: Very good. But the relentless pressure from Disney to never grow up could finally make her snap.

Low point: Vanity Fair incident.

The Gawker Wasted 20Kate Moss, model

The Gawker Wasted 20

How drunk: Modestly, and only via booze. Yay!

Latest: On the one hand, she's reportedly engaged to be married, practicing yoga and tending to her fashion line. On the other, she looked scary and strung out in the last of these February pictures, and sometimes will randomly go without underwear. In March, she had a "boozy lunch" in Paris and then licked her boyfriend's neck.

Outlook: Good. She's avoided any public cocaine relapses over the past three years, though clearly drinks sometimes. She should be further grounded by continuing to raise her daughter, six, and by a reported engagement to guitarist Jamie Hince.

Low point: In 2005, was famously photographed by British tabloid the Daily Mirror snorting cocaine at a recording session for Babyshambles, band of her junkie boyfriend Pete Doherty. She was subsequently dropped by both Chanel and Burberry and entered rehab.

The Gawker Wasted 20Courtney Love, singer

The Gawker Wasted 20

How drunk: Epically.

Latest: Despite recently handing out sobriety advice to Lindsay Lohan and Britney Spears and declaring herself rehabbed, Love was spotted in London this spring looking drunk and carrying copious prescription drugs, which she has abused in the past.

Outlook: Poor. Love insists she's reformed but somehow few people are convinced.

Low point: So many to choose from! Probably the time she thought she was going to die so her hangers-on, according to Love, stole $20 million.

The Gawker Wasted 20Lindsay Lohan, actress (at one point, apparently)

The Gawker Wasted 20

How drunk: Constantly, visibly and criminally.

Latest: Accused of stealing someone else's fur coat from a nightclub. Also recent: getting plastered with her girlfriend at Hawaiian Tropic Club, falling limply while trying to get into a car outside a Hollywood.

Outlook: Surprisingly pretty good. She's getting good report cards on the set of her new movie, and is a newly minted femme lesbian.

Low point: When walking medicine cabinet Courtney Love told her she really needed to shape up. Also: five car incidents in three years, including one where she was alleged to have been chasing someone in her car while drunk.

The Gawker Wasted 20Naomi Campbell, abusive supermodel

The Gawker Wasted 20

How drunk: Unconvincingly reformed.

Latest: Campbell is trying to redeem herself following a spitting, racial-epithet-hurling attack on police at Heathrow airport. She bought coffee for cast members of TV show Ugly Betty and smiled at Heathrow police.

Outlook: Poor. Campbell has falsely claimed to be reformed in the past. In 2006, Campbell told W magazine, "Some people can handle a drink or a line of cocaine, but I've finally come to realize that, for me, it's all or nothing - and it has to be nothing." She was later photographed drinking wine at dinner.

Low point: In 2006, after being arrested for her latest cell-phone beating of the help, she was forced to scrub toilets as part of a community service sentence. She claimed the experience was sobering before moving on to further meltdowns.

The Gawker Wasted 20Pat O'Brien, TV host

The Gawker Wasted 20

How drunk: Freshly rehabbed, working again — for the second time.

Latest: Entered rehab in February (his last rehab had been in 2005). Despite speculation to the contrary, he returned to his hosting gig on The Insider.

Outlook: Weak, since he has relapsed once before.

Low point: A drunken, horny voice mail left prior to his most recent rehab stint.

The Gawker Wasted 20Paris Hilton, attention-mad socialite

The Gawker Wasted 20

How drunk: Very, but in a totally older, more responsible way.

Latest: Hilton now says she's become more domestic, staying home (heavens!) some nights and even cooking dinner for serious boyfriend and rocker Benji Madden. She's taken to wearing a diamond ring on her wedding ring finger and reportedly even talks of children.

Outlook: Precarious. Marriage and increased sobriety are possible; more likely is a breakup and total Hilton meltdown. The starlet has failed at reform before: The Times in March reminded everyone that Hilton still had not taken a charity trip to Rwanda or set up a transitional home for women, as promised on Larry King Live following a jail term.

Low point: Was sent to jail for repeatedly driving on a license suspended in connection with a drunk driving conviction. Runner up: When her cat was reclaimed for alleged neglectful treatment.

The Gawker Wasted 20Nicole Richie, actress, fashion plate

The Gawker Wasted 20

How drunk: Minimally.

Latest: Richie gave birth in January and subsequently said her daughter and relationship to boyfriend Benji Madden, the girl's father, gave her life new meaning and helped her "move on" from her wilder days. Richie's friend Paris Hilton is said to be hoping for a similarly grounding relationship with her boyfriend, Benji Madden, brother to Joel.

Outlook: Decent. Richie raised $1 million by selling pictures of her baby, and her dad Lionel is rich, so she's well funded to either raise a family or have a Britney Spears-style post-baby meltdown. She's 26 so the chance of the latter is not insignificant. But there are no immediate warning signs.

Low point: In 2003, was arrested for possession of heroin. Runner-up: Becoming dramatically thing after a falling out with party buddy Paris Hilton and a brief jail sentence on drunk driving charges.

The Gawker Wasted 20Britney Spears, wayward singer

The Gawker Wasted 20

How drunk: Only on Frappuccinos (this month).

Latest development: Spears is back in the recording studio, has appeared in repeated successful TV cameos and gained new visitation rights with her two sons after a court commissioner said he was "extremely impressed" with her progress.

Outlook: Good, for now. With her father in control of her money and many aspects of her life, Spears is unlikely to backslide anytime soon, particularly given how much she wants to regain custody of her kids. The question is whether she'll be able to stay sober once she has her kids back and is in full control of her bank account.

Low point: Flashing her vag to paparazzi in 2006 while clubbing with Paris Hilton. Runners up: Her two psych-ward stays this year; brief, recent relationships with scuzzballs Adnan Ghalib and Sam Lutfi; shaving her head and bashing a car with an umbrella.

The Gawker Wasted 20Robert Downey, Jr., actor

The Gawker Wasted 20

How drunk: Stone cold sober.

Latest: Downey's film Iron Man has been a critical and financial success, with Downey now expected to take part in sequels. He appears in blackface in the forthcoming comedy Tropic Thunder with Ben Stiller

Outlook: No reason to think he's anything but clean and sober from here on out. Unless you've heard something. What, have you heard something??

Low point: In 2000-2001, when a series of arrests saw him kicked off the hit TV show Ally McBeal. Struggled with drug abuse throughout the 1990s, and eventually served at least a year and a half in jail and several years on probation and in drug treatment.