1 of 15
Jail Stay: 13 days and counting
The actress followed her summer 2010 jail stay for violating probation in a DUI case with 23 days in court-ordered rehab. "I want my career back," Lohan, 24, pleaded in a recent Vanity Fair interview – only to suffer from a major "setback": she tested positive for drugs in a court-mandated test, landing her back in the slammer for less than 14 hours before posting bail.
2 of 15
Jail Stay: 23 days
With hair extensions intact, the heiress "was basically in the fetal position" during her 2007 stay at L.A.'s Century Regional Detention Facility for driving with a suspended license. Upon release, Hilton vows to be "a good person" (she devoured self-help books and the Bible during her stay), but soon returns to her old ways – most recently pleading guilty for cocaine possession in Las Vegas.
3 of 15
Jail Stay: 10 months
Locked up for weapons possession, the rapper endured a seven-month prison stay. He's since used his "humbling experience" to discourage at-risk teens from a life of crime, but still hasn't eluded the law: T.I. was arrested again on drug charges in September with wife Tameka in West Hollywood.
4 of 15
ROBERT DOWNEY JR.
Jail Stay: nearly 1½ years
"When the door clicks shut, then you are safe," says the Golden Globe winner, whose drug-related antics land him in jail intermittently between 1996 and 2001. Dumped from TV's Ally McBeal, a clean-and-sober Downey makes a hero's return nearly a decade later, bringing in more than $100 million in Iron Man's opening weekend in 2008 – a comeback he credits to his wife, movie producer Susan Levin.
5 of 15
Jail Stay: 33 days
The '80s proved one long temper tantrum for the future double Oscar winner – and Madonna's then-husband! The actor – already infamous for tussling with photographers – landed behind bars in '87 after hitting an extra on set and driving recklessly. Decades later he again lashes out at a paparazzo, netting him three years' probation and anger management sessions in 2010.
6 of 15
ZSA ZSA GABOR
Jail Stay: 3 days
Pulled over for expired registration tags in 1989, Gabor stepped out of her Rolls-Royce and slapped a Beverly Hills police officer across the face. Guilty of assault, she spends a weekend in jail. "I admit I have a Hungarian temper," says Gabor, who later spoofs herself in 1991's The Naked Gun 2½. "We are descendants of Genghis Khan and Attila the Hun."
7 of 15
8 of 15
Jail Stay: 8 days
In 1926, the voluptuous starlet writes and stars in the raunchy Broadway revue Sex (about a prostitute plotting to marry a rich man) – and gets thrown into an N.Y.C. jail on obscenity charges. "If I wanted local color," she says upon release, "I sure got it in that place." The scandal only helps elevate her sex kitten persona, launching the campy performer into silver screen stardom.
9 of 15
Jail Stay: 5 months
With a new knit poncho on her back and her daughter Alexis at her side, the domestic diva emerges from West Virginia's Alderson Federal Prison Camp in March 2005, after serving half her sentence for conspiracy and obstruction of justice. "Certainly, there is no place like home," says Stewart, who spends the next five months on house arrest before successfully returning to her lifestyle empire.
10 of 15
Jail Stay: 48 days
The Emmy-winning 24 star serves his entire sentence for a second drunken driving conviction and a probation violation in 2007. After unveiling his star on the Hollywood Walk of Fame, Sutherland returned to his boozing and brawling ways in May 2009, infamously headbutting a fashion designer at an N.Y.C. party.
11 of 15
Jail Stay: 60 days
The Hollywood rebel is caught allegedly smoking marijuana at actress Lila Leeds's home in August 1948, landing him in jail after a sensationalized trial. RKO studio head Howard Hughes sticks behind Mitchum, whose reefer madness (which was later expunged from his record) ups his bad boy ante until his death in 1997 at age 79.
12 of 15
Jail Stay: 17 days
After violating an extended probation, the Lost star – who was busted in '05 for drunken driving in Hawaii after a DUI and a hit-and-run conviction in 2004 – serves a fraction of her 180-day sentence. Although she was killed off from Lost, the tough-chick actress made a blockbuster return in 2009 with Avatar.
13 of 15
Jail Stay: nearly 10 months
Convicted of lying to a federal grand jury about a 2005 shootout, the rapper – who releases her hit album The Naked Truth while incarcerated – receives an early release from a Philadelphia detention center in July '06. She later pays homage to her cellmates by appearing on Dancing with the Stars in '09. "Me and my girls used to watch it," she tells PEOPLE, "and they would say, 'You need to be on that show.'"
14 of 15
Jail Stay: 17 days
After failing to report $180,000 to Italian tax authorities, the legendary screen siren spends a little more than two weeks in a pink cell just outside Naples. The 1982 imprisonment "left a scar," says Loren, but her career was relatively unscathed: She received an honorary Oscar in 1991 and shined in the 2009 movie-musical Nine.
15 of 15
Jail Stay: nearly 3 hours
The Keeping Up with the Kardashians star is sentenced to 30 days in jail after failing to complete roadside cleanup duty and enroll in an alcohol education class on a 2007 DUI charge. A year later, she nabs an E! spin-off, Khloe & Kourtney Take Miami, and marries L.A. Laker Lamar Odom.