The following article includes references to addiction and child abuse.
Prison — the long-term equivalent of jail reserved by the American judicial system as a response for serious violations of criminal law — is theoretically supposed to be a punishment against the offender, but also rehabilitative and a deterrent to the community at large. That’s because even the idea of incarceration can be absolutely frightening; movies and TV shows have consistently shown it to be a dark, stark, joyless, and harsh place, a fitting home for the people who conventional wisdom states did something to deserve their residency there.
To many Americans, the incarcerated population is a great swath of the other — an entire class or collection of people with whom they think they’ll have no interaction and operate in what’s almost a different reality. But so many people have served time in a prison that they’re just one degree away from some of the U.S.’s most celebrated actors, musicians, models, and other famous people. Here are some Hollywood and entertainment elites whose lives were touched by the penal system because one of their parents was imprisoned at some point.
Woody Harrelson's father killed for money
Woody Harrelson came onto the Hollywood radar in the mid-1980s, when he joined the hit show “Cheers” as dim-bulb bartender Woody Boyd. And of all the stellar actors on the NBA mega-hit, it was Woody who went on to the biggest movie career, starring in “The Hunger Games” franchise, “Zombieland,” “Venom,” and “Now You See Me,” and also amassing three Academy Award nominations, most recently for “Three Billboards Outside Ebbing, Missouri.” He played a lawman in that film, as well as in “True Detective,” characters a long way from the real-life exploits of his father.
In The Hollywood Reporter, Woody Harrelson called his father, Charles Harrelson, a “con artist” and a “bad boy” who “made a lot of money gambling.” According to The Guardian, Charles also worked as a contract killer (in other words, a hitman), and he was sentenced to two life sentences for his role in the death of a federal judge based in Texas. Charles Harrelson died in a Colorado penitentiary in 2007.
“He had an incredible intellect, but he went down the wrong path,” Woody said in The Hollywood Reporter. “He spent a long time incarcerated for, well, murder. He was incarcerated from ’68 to ’79, and then he got out for a year and was put back in prison and never left.”
Drake's father served five years on drug charges
Easily one of the most successful and influential musicians of the last 15 years — his casual, half-spoken, half-sung delivery of his pop-meets-hip-hop songs has been adopted by a number of contemporaries — Drake has hit the top 10 of the “Billboard” Hot 100 more than 40 times. Even before all that, he was a young star, appearing as Jimmy Brooks for eight years on the enduring Canadian teen drama “Degrassi: The Next Generation.”
Born Aubrey Drake Graham, the future superstar was primarily raised by his mother, Sandi Graham. When Drake was five, his parents divorced and his father, professional musician Dennis Graham (he once worked as Jerry Lee Lewis’s drummer), relocated back to his hometown of Memphis and started selling narcotics, according to DJBooth. “I didn’t have a father, because he was in jail two separate times,” Drake told Complex in 2011, adding that his dad served two separate stints behind bars.
Leighton Meester was born to a mother serving a federal sentence
Leighton Meester has been in a lot of movies and TV shows — most recently the ABC sitcom “Single Parents” — but she’ll likely also be best known for her role as scheming, wicked private school teen Blair Waldorf on “Gossip Girl,” the premier YA soap of the 2000s and 2010s.
In 2008, Us Weekly reported that members of Meester’s family participated in a drug-smuggling ring before the actor was born. According to Rolling Stone, Meester’s mother, aunt, grandfather, and father were arrested for being involved in a group that brought substantial shipments of marijuana into the United States; her mom, Connie Meester, “was sentenced to 10 years at a federal prison in Texas — at the time, she was pregnant with Leighton.” After the future TV star was born in a hospital, she stayed with her grandmother while Connie finished out the rest of her sentence.
“It makes me not judge people, especially not for their past,” Meester told Rolling Stone. “Or their parents’ pasts.”
Tobey Maguire's father robbed a bank
In the late ’90s and early 2000s, it seemed like Tobey Maguire was linked to almost every prominent movie. He was in a lot of them, including such well-received fare as “Pleasantville,” “Seabiscuit,” “Wonder Boys,” and “The Cider House Rules.” Maguire was pushed into superstardom with his dual role as Spider-Man and his mild-mannered alter ego Peter Parker in three blockbuster “Spider-Man movies” between 2002 and 2007. He earned millions for portraying a big-screen superhero, which is the polar opposite financial situation faced by Maguire’s father in 1993.
That year, Tobey Maguire scored his first major film role in the drama “This Boy’s Life.” His father, Vincent Maguire, according to The Independent, robbed a bank in his hometown of Reseda, California. According to a source close to the Maguire’s who spoke to the National Enquirer, Vincent Maguire’s sister had recently died from cancer, and he had been diagnosed with polyps, but he was convinced that he had cancer, too. That, along with taking custody of his sister’s two children and not knowing how he would afford to raise them, sent Vincent to the Coast Federal Savings branch across the street from his home. According to the National Enquirer’s tipster, “Vincent walked into the bank, presented the teller with a note demanding the money and indicated he had a weapon in his pocket.” He was not actually armed, but the teller obliged. Police captured him shortly after. Vincent Maguire pleaded guilty and spent two years in prison.
Keanu Reeves' father was imprisoned for selling heroin
Everyone loves Keanu Reeves, but everyone’s got a different reason, be it from any line item on his resume, such as “Bill and Ted’s Excellent Adventure,” “The Matrix,” “Speed,” or “John Wick.” But for as much joy as Keanu Reeves has brought the world, his personal life has been characterized by pain: According to People, his girlfriend Jennifer Syme gave birth to a stillborn baby in 1999 and died in a car accident the following year.
Keanu also had a difficult relationship with his father, Samuel Reeves. As Rolling Stone chronicled in their 2000 interview with the actor, the elder Reeves met costume designer Patricia Taylor and fell in love, and they had Keanu in 1964. Samuel left the family when the future star was, leaving Keanu’s mother to raise her kids alone. Reeves believes the last time he saw his father in person was when he was 13, around 1978.
In 2001, Samuel Reeves told the Honolulu Star-Bulletin that despite his efforts to get in touch with his son, he hadn’t been successful, believing that the distance was the result of his decades-long struggle with heroin addiction. As the publication recounted, Samuel was arrested at Hilo Airport in Hawaii attempting to sell the drug in 1992, and he served two years of his 10-year prison sentence. According to the National Enquirer, Samuel died in 2018 and Keanu didn’t attend the memorial service.
If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA’s National Helpline at 1-800-662-HELP (4357).
Terrence Howard's father stabbed a man in a line to see Santa Claus
Terrence Howard is an intense actor who has appeared in a variety of projects. He reached the Hollywood A-list in 2005 with the role of Djay, a criminal and aspiring musician in “Hustle and Flow,” which earned him an Academy Award nomination and set him off on bigger things, like portraying James “Rhodey” Rhodes in “Iron Man” and starring on the Fox record industry soap “Empire.” Not so glorious: One of his earliest memories is of a violent and shocking incident involving his father. According to The New York Times, the Howard family — Terrence, his two brothers, and parents, Tyrone and Anita — headed into downtown Cleveland just before Christmas in 1971 to visit Santa Claus at Higbee’s department store. Witness accounts vary, but John Fitzpatrick reportedly accused Tyrone Howard of cutting in life, which led to a physical altercation. Anita Howard said Fitzpatrick kicked her husband in the groin multiple times, but when it was all over, Fitzpatrick was dead from multiple stab wounds delivered with a nail file, according to Rolling Stone.
“I was standing next to my father, watching,” Howard said in Rolling Stone. “Then stuff happened so quickly — blood was on the coats, on our jackets — and then my dad’s on a table and then my dad is gone to prison.” As the outlet noted, following the incident, which was dubbed the “Santa Line Slaying,” Tyrone Howard served 11 months in prison.
Lindsay's Lohan's father went to prison a few times
Actor and pop singer Lindsay Lohan has had a few legal problems over the years. According to E! News’ roundup of her arrests, she pleaded guilty to cocaine use and driving under the influence (leading to a slew of probation violations, missed court dates, and revoked bail issues) in 2007 — and that was one of the many times she ended up in front of a judge. The four-time Teen Choice Awards and three-time Razzie Awards winner isn’t the only Lohan with a file in the U.S. penal system. The actor’s father, Michael Lohan, has a prison record going back several decades. After working as a stock trader in New York, the patriarch of the Lohan family was investigated on suspicion of insider trading and in 1990 sentenced to three years in prison on a contempt of court charge (for refusing to testify against other brokers), according to the New York Observer. The outlet went on to note that four years after his release, Lohan was sent back behind bars for a year when he violated his probation by flying to California after daughter Lindsay was hospitalized for an asthma attack.
Other legal issues include being charged with assaulting his brother-in-law in 2004, which, as CNN reported, landed him back in a New York state prison once more in 2005, and for more than two years, after a conviction for attempted assault and driving without a license, according to CBS News.
Kane Brown's father and stepfather spent time in prison
Kane Brown was on the verge of fame for a while before he finally hit it big in country music with songs like “Lose It,” “What Ifs,” and “Heaven.” He tried out for “American Idol” without success and he walked away from “The X-Factor” in 2013 after producers wanted to make him part of an assembled boy band, according to Yahoo! Life. As he told Billboard, his music career really got off the ground while he was working at FedEx and sharing country covers on YouTube. Not before long, he was a viral sensation with a record deal and in 2017 he became the first artist to ever simultaneously top all five of the Billboard country music charts.
When Brown was about three years old, in 1996, his father was sent to prison, where he remains. “He brags about me and talks about how good he is on the drums,” Brown said in Billboard. “I always joke with him and say that I’m going to hire him when he gets out.” Brown’s mother coupled with another man early in her son’s childhood, and the singer-songwriter detailed his relationship with that stepfather in “Learning.” In the lyrics, Brown recounts how after wetting the bed as a six-year-old, his stepfather abused him. When his grandmother figured it out, he sings that “she had him locked in a cell.” He told Taste of Country, “My nana was a detective, my nana was a great cop.”
If you or someone you know may be the victim of child abuse, please contact the Childhelp National Child Abuse Hotline at 1-800-4-A-Child (1-800-422-4453) or contact their live chat services.
Hope Solo is the result of a conjugal visit
Hope Solo is one of the most decorated soccer players in American history. Serving as the goaltender for the U.S. women’s national team for 16 years, she won two Olympic gold medals and a World Cup. Her tenure at the top was not without controversy, per The Guardian, as she was suspended from the U.S. team for 30 days after her husband, Jeremy Stevens, got a DUI. She was also charged with assault after a scuffle with family members in 2014; according to AP, the charges were dropped.
Hope grew up in Richland, Washington, not far from the Washington State Penitentiary in Walla Walla, where Jeffrey John Solo, a former employee of the Lockheed-Martin aircraft manufacturing company, was residing after being convicted of embezzlement. The superstar athlete was conceived while her father was locked up. In “Solo: A Memoir of Hope,” she writes, “Toward the end of my father’s sentence, she married him and became pregnant with me.”
Tyga's father has been in prison since he was a toddler
Michael Ray Nguyen-Stevenson is far better known by his stage name: Tyga. The rapper has sold millions of albums and downloads and scored lots of major hits, including “Taste,” “Faded,” and “Rack City.” But Tyga might be even better known for his personal life. After having a son with model Blac Chyna, he dated reality TV superstar Kylie Jenner for about a year.
In March 2016, the rapper shared on Twitter a letter sent by his biological father, Stevie J. Stevenson, marking the 25th anniversary of his incarceration, which Tyga noted was a life sentence. He also revealed that he’d never physically met the man. In an interview on public radio station KALW, Stevenson attested that he was in the delivery room when Tyga was born in 1989, but lost contact shortly after, and he began serving life without the possibility of parole — on kidnapping and drug charges — in 1991. He’s currently incarcerated at Solano State Prison in California.
Kimora Lee Simmons's father did time for corruption and drugs
Starting out as a teenage model in the 1980s for Chanel and as an inspiration for Karl Lagerfeld, Kimora Lee Simmons started her rise to the top of the fashion world early. She’d go on to steer Phat Farm, the popular men’s clothing line marketed by then-husband record executive Russell Simmons, and then launch her own spinoff called Baby Phat. Simmons also starred on the reality show “Kimora: Life in the Fab Lane” and won a Tony Award for producing “Def Poetry Jam” on Broadway.
Simmons got off to a rocky start. Born in St. Louis, she told the Sydney Morning Herald that she “was an oddity” and not accepted by her peers because of her biracial background. She also came from a prominent family split apart by scandal. As the outlet noted, Simmons’s father, Vernon Whitlock, Jr. was the first Black man to work as a Deputy Federal Marshal for the city of St. Louis. After more than a decade in service and civil service, according to The Guardian, Whitlock became a bail bondsman, where he reportedly started engaging in illegal things. In 1985, an investigation turned up evidence that Whitlock had traded bonds for jewelry or sexual favors and had also dealt cocaine and synthetic heroin. Whitlock was sentenced to 24 years in prison, but was released after three after he agreed to reveal the name of his drug supplier.
Kellie Pickler's father was in and out of jail
Kellie Pickler has found quite a bit of success. She was a high-finisher on the 2006 season of “American Idol” (placing sixth and losing to Taylor Hicks), she won her season of “Dancing with the Stars” in 2013, and co-hosted the talk show “Pickler and Ben” for two years. She’s done pretty well off TV, too, taking five songs to the upper reaches of the Billboard country chart.
According to AARP, Kellie was primarily raised by her paternal grandparents in Albemarle, North Carolina, after her mother left her daughter with Clyde “Bo” Pickler, a man who was in and out of prison. After Kellie grew up and found fame, he continued to get in trouble with the law. According to TMZ, Bo Pickler spent 2003 to 2006 in a Florida institution after stabbing a neighbor, and in 2007, he was arrested in North Carolina for attempting to sell stolen cars. The elder Pickler was picked up by police again in 2016 for selling marijuana, according to the Island Gazette, and he died in 2019.
The father of St. Vincent singer Annie Clark did jail time for financial crimes
One of the most daring, audacious, and experimental performers in modern rock, Annie Clark performs under the name St. Vincent. More of a performance artist than a typical rock singer, St. Vincent has topped critics’ lists for albums like “Masseducation” and “St. Vincent,” the latter of which won the Grammy for Best Alternative Album.
According to the U.S. Department of Justice, in 2010, her father, Richard Clark, received a 12-year prison term for participating in a stock manipulation scheme that netted $43 million in ill-gotten funds. (According to the DOJ, “Clark was found guilty on one count of conspiracy, seven counts of wire fraud, five counts of securities fraud and one count of money laundering.”) The Guardian noted that Annie “never discussed her father’s imprisonment until the tabloids dug it up in 2016” because she wanted to shield her underage siblings from media attention and scrutiny. “I wasn’t in any kind of place where I wanted that narrative to overshadow the music,” she told the outlet. In 2021, Annie Clark released the St. Vincent album “Daddy’s Home,” with a title track about the singer-songwriter picking up her father from prison upon his early release in 2019.
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