10 Celebrities Who Regret Their Past

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Welcome to WatchMojo, and today we’re looking at celebrities who openly regret their troubled, reckless, or scandalous past.

Al Pacino

Before becoming one of Hollywood’s greatest actors, Al Pacino endured a difficult youth - especially during his time in Italy. The “Godfather” actor has since revealed that, at around 20 years old and struggling in Sicily, he “sold his body” to an older woman in exchange for food and a place to stay. Reflecting on this time, Pacino admitted it left him waking up “not really loving himself,” as the memory carried a heavy sense of shame. Now, the veteran actor is widely celebrated as a screen legend, but his candid and vulnerable admission shows just how far he had to climb to reach the top.

Kristen Stewart

“Twilight” star Kristen Stewart hasn’t shied away from expressing deep regret over her past behavior. This is especially true of her 2012 affair with “Snow White and the Huntsman” director Rupert Sanders, which occurred while she was dating Robert Pattinson. At the time, Stewart issued a highly public and emotionally charged apology, stating she deeply hurt Pattinson and regretted her “fling” with the director. She further revealed that the betrayal lit her “universe on fire,” illustrating the emotional fallout that followed her. Stewart has since rebuilt her reputation with acclaimed indie and arthouse projects. She’s also openly embraced her queer identity, refusing to let past regrets hold her back in any way.

Drew Barrymore

Just how chaotic was Drew Barrymore’s childhood? The Hollywood star was drinking by age nine, partying at Studio 54 before most kids hit middle school, experimenting with illicit substances at twelve, and was sent to psychiatric rehab at just thirteen. While Barrymore sees her turbulent past as a key part of her resilience and doesn’t outright regret it, she admits she still “hasn’t forgiven herself’ for certain chapters of her upbringing. She also admits that these experiences have made her especially hard on herself as a parent. Now a stable force in showbusiness, the actress-turned-talk-show-host’s story reflects not so much regret as transformation - turning past chaos into a platform for growth.

Shia LaBeouf

Shia LaBeouf’s life and career has been marred by a seemingly endless string of scandals - from plagiarism allegations, arrests, abuse claims, and public outbursts. LaBeouf has gone on to publicly apologize for his past behavior, even describing himself as “pleasure-seeking, selfish, self-centered, dishonest, inconsiderate, and fearful.” He’s expressed that he especially holds deep shame over his abusive behaviors. The actor has cited Catholicism and sobriety as lifesaving, stating he felt “depraved” and needed redemption through faith. Shia is still attempting to rebuild his reputation by engaging in introspective art, confronting his mistakes, and publicly seeking forgiveness.

Michael Richards

It’s no secret that Michael Richards’ career imploded in 2006 when a video surfaced of him unleashing a racist tirade at hecklers during a stand-up set at The Laugh Factory. While he deeply apologized, admitting his words were hateful, the damage was already done. Richards has since candidly acknowledged that the incident remains his greatest personal and professional regret. In later reflections, including in his memoir, the comedian also revealed he regretted taking his role on “Seinfeld” so seriously, saying he became consumed by the pressure of living up to Kramer’s success. He admitted that the combination of ego, stress, and anger contributed to his overall meltdown.

Mike Tyson

Boxing legend Mike Tyson has repeatedly expressed regret for his violent and erratic behavior throughout his career as a pro fighter. Beyond his 1992 conviction of indecent assault, Tyson has admitted shame over his public outbursts and how he treated fellow fighters, including biting Evander Holyfield’s ear during a 1997 match. Iron Mike has said that his substance use and anger issues led him down destructive paths that hurt both himself and others. He shared in interviews and his autobiography that his arrogance and lack of control nearly ruined his legacy. Today, Mike Tyson often speaks about his past mistakes with honesty, framing them as hard-learned lessons.

Mark Wahlberg

As a teenager in Boston, Massachusetts in the mid-to late-80s, Mark Wahlberg was involved in violent, racially motivated crimes - including assault and hate crimes. Things got so bad for Marky Mark, that he ended up serving jail time for an attack on a Vietnamese man in 1988. Wahlberg has since openly stated that he made “a lot of terrible mistakes” in his past and is striving to correct those errors. In fact, today, the actor is involved in many philanthropic efforts - especially youth support organizations. Wahlberg’s transformation from troubled youth to industry leader reflects deep introspection and a commitment to redemption. It’s clear he’s since taken up trying to lead by example.

Hugh Grant

Hugh Grant’s infamous 1995 arrest on the Sunset Strip for lewd conduct with a sex worker (Divine Brown) came just days before the major film release of “Nine Months.” Making headlines worldwide, Grant has called the incident “a moment of insanity.” And while he weathered the scandal with grace and charm, even delivering one of the more well-received celebrity apologies opposite Jay Leno on “The Tonight Show,” he continues to acknowledge his past behaviour. The scandalous arrest has since become a cautionary tale about fame and impulse. And luckily for the sheepish English actor, he’s been able to rebuild from it.

Charlie Sheen

Charlie Sheen’s career was once defined by monumental success, but it nearly collapsed under the weight of his addictions and reckless behavior. Charlie’s battles with substance abuse led to multiple stints in rehab, arrests, and a notorious firing from “Two and a Half Men” after his highly public meltdown. Sheen soon became infamous for his erratic interviews and appearances, turning him into a tabloid spectacle. Looking back, the actor has admitted to being deeply ashamed of his past, even saying he suffers from “shame shivers” when reflecting on his self-destructive choices. Today, Sheen openly regrets the pain his actions caused his family and career - acknowledging that his substance use and arrogance nearly destroyed everything.

Robert Downey Jr.

To say Robert Downey Jr. endured a tumultuous period in the 1990s would be an understatement. Marred by multiple arrests for drug possession, a year in prison, and being widely considered un-hirable, RDJ’s life was spiraling out of control. The “Iron Man” actor has since turned his life around however, achieving one of the most remarkable and inspiring comebacks in Hollywood history. Expressing gratitude for the second chance he was given, Downey Jr. would ultimately receive a pardon for his drug-related offenses, enabling him to serve on a jury and symbolically close that chapter from his past. Since 2003, Downey has maintained sobriety, crediting his wife Susan, therapy, yoga, and martial arts with his recovery.

Which celebrity’s past surprised you the most? Share your thoughts in the comments down below.