Actors who Served Prison Time

Some big-name actors have spent time behind bars—sometimes long before their breakout roles, sometimes in the middle of busy careers. Their cases range from tax offenses to violent crimes, and the outcomes reshaped personal lives and professional paths in very different ways.

Below, you’ll find well-known male performers who served prison sentences, along with concise context about their work. For each, we’ve included nuts-and-bolts details about notable films or shows—plots, cast, and crew—so you can place their careers next to the timelines of their legal troubles.

Robert Downey Jr.

Robert Downey Jr. was sentenced in August 1999 and served roughly a year at the California Substance Abuse Treatment Facility and State Prison, Corcoran, after repeated probation violations tied to drug possession; earlier court actions and releases marked a turbulent period that bookended his incarceration. Professionally, his mainstream resurgence arrived with Marvel’s ‘Iron Man’—directed by Jon Favreau and co-starring Gwyneth Paltrow and Jeff Bridges—which established Tony Stark as the quip-driven center of an interconnected superhero franchise built around engineers, A.I., and weapons-industry morality.

Before that comeback, Downey had headlined ‘Chaplin’, a biographical drama directed by Richard Attenborough that follows Charlie Chaplin’s rise from vaudeville to silent-film icon through studio politics, censorship battles, and personal scandal; the supporting cast features Geraldine Chaplin, Dan Aykroyd, and Anthony Hopkins, with period-authentic production design and a score that mirrors Chaplin’s blend of slapstick and sentiment.

Wesley Snipes

Wesley Snipes reported to the Federal Correctional Institution McKean in December 2010 to serve a three-year sentence after convictions for failing to file federal income tax returns; he began his term after unsuccessful bids to avoid incarceration and completed supervised release after serving time. His signature action-horror vehicle ‘Blade’—directed by Stephen Norrington and produced by Peter Frankfurt, Wesley Snipes, and Robert Engelman—casts him opposite Kris Kristofferson and Stephen Dorff in a story about a human-vampire hybrid waging a stylized war against bloodsuckers, blending martial-arts choreography with comic-book lore and nightclub-neon world-building.

Beyond that franchise, Snipes co-led the street-ball comedy-drama ‘White Men Can’t Jump’, written and directed by Ron Shelton, where his hustling character partners and clashes with Woody Harrelson on the blacktop; the film weaves locker-room banter and relationship stakes—anchored by Rosie Perez—into a con-game rhythm that drives its Venice and Watts pickup-game set pieces.

Tim Allen

Tim Allen served about 28 months at the Federal Correctional Institution in Sandstone, Minnesota, following a 1978 arrest for transporting cocaine; he had faced a potential life sentence before cooperating with authorities, then paroled after serving a portion of the federal term. On television he became widely known for ‘Home Improvement’, an ABC multi-camera sitcom created by Carmen Finestra, David McFadzean, and Matt Williams, with Allen’s tool-show host sharing scenes with Patricia Richardson and Richard Karn in family-and-workplace plots staged on soundstages and a within-the-show workshop.

On the film side, Allen voiced Buzz Lightyear in Pixar’s ‘Toy Story’, directed by John Lasseter with a cast that includes Tom Hanks, Don Rickles, and Annie Potts; the buddy-adventure plot follows toys navigating jealousy, rescue missions, and a suburban move, while digital animation, Randy Newman’s songs, and a lean screenplay structure the toy-box world. He also fronted ‘The Santa Clause’, a family fantasy directed by John Pasquin that pairs office-party gags with North Pole production design and an ensemble of elves, neighbors, and ex-spouses.

Danny Trejo

Danny Trejo served time in California prisons—including San Quentin—where he boxed and later connected with screenwriter and ex-convict Edward Bunker; after release, a set visit led to work on ‘Runaway Train’, a Cannon Group thriller directed by Andrei Konchalovsky and starring Jon Voight and Eric Roberts as escaped inmates aboard an unmanned locomotive, with Trejo contributing boxing training and appearing in prison sequences that frame the film’s survival-on-steel premise.

As a leading man, Trejo headlined Robert Rodriguez and Ethan Maniquis’s ‘Machete’, an exploitation-style action film that casts him opposite Michelle Rodriguez, Jessica Alba, and Robert De Niro, following an ex-federale pulled into a web of double-crosses, border vigilantism, and campaign-trail violence; earlier, he appeared in Michael Mann’s ‘Heat’, a heist drama built around Al Pacino and Robert De Niro, where disciplined crew logistics, LAPD tactics, and a downtown shootout drive the cat-and-mouse plot.

Stephen Fry

Stephen Fry served three months as a teenager at Pucklechurch Prison for credit-card fraud; after his release he returned to education and eventually joined the Cambridge Footlights, a path that preceded screen roles and collaborations with Hugh Laurie. Among his notable performances is ‘Jeeves and Wooster’, adapted from P. G. Wodehouse’s stories, where Fry plays the unflappable valet opposite Laurie’s affable Bertie in farcical episodes written and produced for television with period costumes, clubland slang, and a revolving door of aunts, fiancées, and mix-ups.

Fry also portrayed Oscar Wilde in ‘Wilde’, a Brian Gilbert-directed biopic that traces the playwright’s romance with Lord Alfred Douglas and the court cases that followed; the production casts Jude Law, Vanessa Redgrave, and Jennifer Ehle, staging salons, courtrooms, and domestic scenes that follow the arc from literary acclaim to legal downfall.

Charles S. Dutton

Charles S. Dutton served multiple Maryland sentences beginning with a manslaughter conviction and later terms linked to robbery and a prison altercation; he discovered acting while incarcerated, organizing a drama group and pursuing formal training after release. He later starred in the Fox series ‘Roc’—created by Stan Daniels and produced by HBO Independent Productions—playing a Baltimore garbage collector opposite Ella Joyce and Rocky Carroll in neighborhood-grounded stories filmed on multi-camera stages, including live-to-air episodes that showcased theater-caliber timing.

On film, Dutton’s credits include ‘Alien 3’, David Fincher’s bleak sci-fi thriller that strands Sigourney Weaver’s Ripley on a penal-colony planet where monastic inmates face an evolving xenomorph, with ensemble performances from Dutton, Charles Dance, and Paul McGann; he also appeared in ‘A Time to Kill’, based on John Grisham’s novel, where director Joel Schumacher stages a Mississippi courtroom drama anchored by a defense-team ensemble and racially charged jury dynamics.

O. J. Simpson

O. J. Simpson served nearly nine years in the Nevada Department of Corrections after convictions for armed robbery and kidnapping tied to a Las Vegas memorabilia confrontation; he was paroled and released in October 2017 following a widely covered hearing that assessed conduct, risk factors, and the specifics of the offense. As an actor, Simpson is well known for the comedy ‘The Naked Gun’, directed by David Zucker and derived from the ‘Police Squad!’ TV format, where he appears alongside Leslie Nielsen, Priscilla Presley, Ricardo Montalbán, George Kennedy, and others in a spoof built around slapstick investigations, mind-control assassination plots, and deadpan line-delivery.

Across the series, the production’s gag density, stunt-driven set pieces, and running bits—stadium chaos, press-conference pratfalls, and lab-gadget demonstrations—frame Nielsen’s Frank Drebin as the anchor, while supporting characters like Presley’s Jane Spencer and Simpson’s Nordberg recur through police-precinct and civic-ceremony backdrops.

Lillo Brancato

Lillo Brancato Jr. was sentenced to ten years in state prison after an attempted-burglary conviction stemming from a Bronx incident in which an off-duty NYPD officer was killed by Brancato’s accomplice; he was paroled after serving time in multiple New York facilities and later resumed screen work. He is closely associated with ‘A Bronx Tale’, directed by Robert De Niro from Chazz Palminteri’s one-man play, where Brancato plays Calogero in a coming-of-age story about a neighborhood kid torn between his bus-driver father’s guidance and a mob boss’s mentorship, with Palminteri, De Niro, and Taral Hicks rounding out the ensemble.

He also appeared on ‘The Sopranos’, David Chase’s New Jersey crime saga built around James Gandolfini’s Tony Soprano and a sprawling cast; the series layers therapy scenes, family meals, FBI pressure, and crew rivalries, employing handheld camerawork and needle-drops to punctuate sudden violence and moral drift across mob storylines.

Michael Jace

Michael Jace is serving a sentence of forty years to life after his 2016 conviction for the murder of his wife; proceedings detailed the shooting and subsequent evidence, with sentencing and appeals reported by Los Angeles outlets and state authorities. On television, he is best known for ‘The Shield’, created by Shawn Ryan, where he played a member of an experimental LAPD unit alongside Michael Chiklis, Walton Goggins, and CCH Pounder; the series uses handheld photography, gritty precinct politics, and inter-agency friction to stage raids, informant flips, and internal-affairs showdowns.

Jace’s film appearances include roles in ‘The Replacements’, a sports comedy directed by Howard Deutch with Keanu Reeves and Gene Hackman charting a scab-team’s locker-room chemistry during a pro-football strike, and ‘Forrest Gump’, where brief ensemble parts slot into long-span American history vignettes built around Tom Hanks’s titular character.

Bill Cosby

Bill Cosby served more than two years of a three-to-ten-year sentence after a 2018 sexual-assault conviction; in 2021, the Pennsylvania Supreme Court vacated the conviction on due-process grounds related to a prior prosecutor’s non-prosecution agreement, and he was released. On television, he starred in ‘The Cosby Show’, created by Bill Cosby with Ed. Weinberger and Michael J. Leeson, centered on the Huxtable family and filmed at Kaufman Astoria Studios with direction by Jay Sandrich and others; the multi-camera production emphasized family banter, school-and-work arcs, and music-inflected opening sequences, with an ensemble including Phylicia Rashad and Malcolm-Jamal Warner.

Earlier, ‘The Bill Cosby Show’ cast him as a Los Angeles physical-education teacher navigating classroom challenges and community ties; Quincy Jones provided the theme ‘Hikky Burr’, and guest stars cycled through standalone episodes, using single-camera staging and location work to distinguish its tone from later studio-audience sitcoms.

Have another name to add, or a film we should spotlight for one of these actors? Share your thoughts in the comments!