Roseanne Barr’s Daughter on Dealing With Mom’s Affair, Secret Daughter, and Racist Tweet

Growing up as the child of a celebrity can be a difficult act to manage. But being the daughter of Roseanne Barr seems to have been a challenge all its own.

Jenny Pentland, Barr’s second child with her ex-husband Bill Pentland, describes her life as a comedy of errors, detailing in her searingly honest memoir This Will Be Funny Later what it was like to have her life strangely mirrored in her mother’s hit 1990s sitcom Roseanne.

But somewhere along the way, the primetime family show took a drastic split from the life Pentland, now 45, was living, and she spent a majority of her teenage years being bounced between abusive behavioral institutions.

Even before she was shuttled off to weight-loss camps, reform schools, and “survival” programs, life under Barr’s roof had been a whirlwind after the comedian inked the deal of a lifetime with ABC. When the show premiered in 1988, Barr became an immediate sensation, pushing her loud, brash lower-middle-class family into the Hollywood limelight.

Pentland’s pre-teen years were soon swept up in the media frenzy over Barr’s divorce from Bill, sparked by The National Enquirer sniffing out her affair with Roseanne writer Tom Arnold. Things only intensified when the tabloid discovered that Barr had a secret daughter whom she had given up for adoption when she was a teen.

The pressure and stress that Pentland associated with her family suddenly being thrust into the spotlight led to her and older sister Jessica rebelling (as any teen would), but escalated when they were placed in various psychiatric hospitals and treatment programs until they were of legal age. (Pentland claimed it was Barbara Walters who first encouraged Barr to consider such facilities.)

But Pentland doesn’t hold a grudge against Barr for her upbringing, detailing her close relationship with her mother and how their family relied on what they considered the most important thing in getting through their troubles: comedy. “Even in the midst of all the shit, being funny was the most important skill you could develop in my family,” she writes.

“You could defuse any situation and tell the most brutal truths without consequence if you could just make everyone laugh. It was a risk, though. If you didn’t absolutely nail the joke, you were fucked.”

Barr has kept a relatively low profile since she blew up her life over a racist tweet directed at Obama aide Valerie Jarrett in spring 2018. The 69-year-old claimed she had taken an Ambien when she compared Jarrett, who is Black, to the “Muslim brotherhood” and “Planet of the Apes” having a baby. (The makers of Ambien issued a statement saying “racism is not a known side effect” of the medication.)

ABC quickly pulled the plug on her freshly revived sitcom, which had premiered two months earlier to record ratings. In a further blow, the network then developed a spinoff of the show, titled The Conners, with most of the cast members from Roseanne returning except for Barr.

Pentland briefly touches on her mother’s meltdown, which occurred while she was traveling with her eldest son for his high school graduation. The scandal unfolded in real time on Twitter and, in the span of a short flight, Barr had gone from trending to unemployed.

It wasn’t surprising that ABC decided to cancel the show, especially because Barr didn’t seem particularly interested in the reboot in the first place, Pentland explains in her book.

“Her internet-trolling, name-calling, conspiracy-theory-based tweets were upsetting to people, and even though her public relations staff and the network suggested she stay off Twitter, she kept at it,” Pentland writes. “She doesn’t like being told what to do, in case we haven’t already established that.”

“I could tell she wasn’t truly invested in the new Roseanne show. Most of her time was spent studying Judaism or watching true-crime programs, and this new attempt at staying relevant in an industry she didn’t much care for seemed more of a burden than a joy. She had sounded exhausted and underwhelmed any time we had talked on the phone recently.”

That’s all Pentland would offer on the subject of her mother’s fall from grace, not daring to wade into Barr’s other tweets that promoted Q-Anon conspiracy theories and rallied behind former President Donald Trump. The last time Barr tweeted was in December 2020, when she encouraged her followers to join her livestream with Overstock founder Patrick Byrne, who she claimed could prove the voting machines in the 2020 election were “fraudulent.” (Barr is still somewhat active on Twitter, recently liking a post from The Babylon Bee which spoke of Democrats having “dirt” on Hillary Clinton.)

It was disorienting for Pentland to have her life somewhat mirrored on Roseanne, admitting it became the bane of her existence when a stranger would annoyingly pester her about which character on the show had been based on her.

“I resented Parallel Jenny’s simple life,” Pentland writes. “I couldn’t watch the show without feeling angry… It still made me sad sometimes to think about what I had missed, but I had a life I wanted now and my pain was dull enough that I could enjoy the truly excellent joke writing.”

I resented Parallel Jenny’s simple life. I couldn’t watch the show without feeling angry… It still made me sad sometimes to think about what I had missed, but I had a life I wanted now and my pain was dull enough that I could enjoy the truly excellent joke writing.

“Neither Becky nor Darlene had to manage a public life because of their mother’s fame,” she continues. “There were no crash diets as they didn’t struggle with their weight… They suffered no PTSD or mental illness in the form of anxiety disorders. Neither of them had been indoctrinated into a cult, OD’d, or spent a year or more in a private mental health facility. They were lightweight, PG versions of us with no complicated backstories. Must be nice.”

Pentland’s life now is miles away from that of her childhood. The mother of five boys, ages 21 to 18 months, she lives in Hawaii with her husband Jeff. They swapped life in Los Angeles for life on an island after Barr decided on a whim to buy a 40-acre macadamia nut farm in 2008 and needed someone to help look after it. The property served as a backdrop to Barr’s short-lived reality show Roseanne’s Nuts in 2011.

Barr’s journey to stardom is a true Cinderella story. Living in a trailer home with three young kids, Barr discovered her passion was entertaining and began performing at local open mic nights in Colorado. It didn’t take long until she was discovered by a talent booker for Johnny Carson, with her debuting on his show in 1985. Her set was spun into a national comedy tour, then an HBO special in 1987, before ABC came knocking.

The sudden fame and success would be a shock to any family, but it seemed to be a particularly hard adjustment for Barr and her children. “In everyone’s perception, we were basically the Beverly Hillbillies,” Pentland writes. “It’s true, we didn’t know how to have money or status or fame or any of the things coming our way, and the people who did know about those things resented our greenness.”

As Barr’s stock began to rise, her relationship with her first husband Bill began to crumble. Things had been strained for some time, but the breaking point was Barr’s affair with Arnold, a Roseanne writer and stand-up comedian. Bill learned of the dalliance when a National Enquirer reporter cold-called him and offered to play him an audio tape of the two lovers spending an illicit night together at her hotel room.

Already heading toward a tabloid scandal, the second blow came when a private detective working for the Enquirer discovered that a teenage Barr had put her infant daughter up for adoption, threatening to turn over the information to the outlet unless Barr forked over $500,000.

Barr decided to pay the hefty blackmail sum to keep the news out of the press and to protect her daughter Brandi, who was about to turn 18. But Barr ended up being scammed, and the Enquirer ended up running the story about Brandi’s existence, along with details about their mother-daughter reunion call.

While Pentland says her parents told her about Brandi, she wasn’t expecting to be confronted with the news in such an intrusive manner, reading about her half-sister in a splashy tabloid one day after school. “The first time I ever saw my sister Brandi’s face was in the prom picture her high school boyfriend shared on the front page of the National Enquirer while I was standing in line at the grocery store,” Pentland writes.

“I knew my mom had found Brandi and talked to her; I knew that there had been foul play and the Enquirer had blackmailed us and bought stories, but it never occurred to me that that is the way I would be introduced to her.”

With the twin scandals of Barr’s divorce and secret daughter unfolding in the press, Pentland and her siblings were caught up in the whirlwind, as paparazzi hounded the family everywhere they went, particularly interested in Barr and Arnold’s highly-publicized romance.

Unbeknownst to Barr at the time, Arnold had been selling stories to the press to fuel his drug habit. Pentland says she inadvertently came face-to-face with her mother’s new boyfriend’s addiction when she visited Barr on the set of She-Devil. Snooping through her mother’s purse, she discovered a tiny vial that contained a white powdery substance. Immediately, even though she was only 12 years old, she knew it was cocaine.

“I was livid,” she writes. “I threw open the door to the trailer, finding my mom standing outside with some wardrobe stylists. I held the vial out self-righteously and said, ‘What is this?’ My mom’s face dropped, and she excused herself to come into the trailer. She shut the door… She told me it was Tom’s. She had taken it from him earlier that day and had nowhere to put it. She was trying to help him get clean. He had a problem, and she loved him and wanted to help. I felt horrible for my reaction. She was just trying to help someone.”

She told me it was Tom’s. She had taken it from him earlier that day and had nowhere to put it. She was trying to help him get clean.

Arnold’s drug addiction was a cause of concern for Pentland’s father Bill, who confided in a close family friend Chai, who happened to be a voodoo priestess. She promised she would “take care of it.” The next month, Arnold overdosed on cocaine and was hemorrhaging.

“When Chai found out that Tom had overdosed and hemorrhaged, she nodded knowingly,” Pentland writes. “She told my dad that she had, just the evening before, ‘pushed’ Tom. She wasn’t causing his abuse issues, she was just exposing them, putting a magnifying glass on them, making them come to a head faster, like putting a hot towel on an abscess. It was an exhausting process but worth it. Now my dad didn’t have to spend money on PIs to prove Tom was on drugs.”

Barr was able to get Arnold into rehab, and he embraced sobriety. Once he got out, Arnold began infiltrating every part of Barr’s life, marrying Barr in January 1990 and, as a splashy 1990 Vanity Fair cover story detailed, ending up having her whole team replaced.

With her mother juggling a successful sitcom, a new romance, and navigating her parents’ custody agreement, Pentland began slowly acting out.

First there were minor acts of defiance, such as joining forces with her siblings to blackmail their nanny. Tired of the healthy food they were forced to eat, Pentland and her siblings convinced their nanny to buy them tubs of sauerkraut, saying they would inform their parents that she had been talking about using the drug PCP if she didn’t.

But Pentland’s sister Jessica went a step further in her rebellious phase, continuously testing the boundaries of her parents’ patience by going on joyrides, drinking underage, and demanding a coffin for a bed. At a loss for what to do, Barr and Bill Pentland decided to stealthily send her to CEDU, a behavioral boarding school in Running Springs, California.

Roseanne Barr, wearing a black outfit, with her children (Brandi Ann Brown, Jake Pentland, Jennifer Pentland, and Jessica Pentland) and partner, Ben Thomas, at the 1994 MTV Video Music Awards, held at Radio City Music Hall in New York City, New York, Sept. 8, 1994.

Vinnie Zuffante/Michael Ochs Archives/Getty

Months later, Pentland was also sent to a similar institution after she started smoking cigarettes, mouthed off to teachers, and her grades slipped. From ages 13 to 18, Pentland bounced around various reform schools, boot camps, and psychiatric hospitals.

During one wilderness boot camp, Pentland was forced to hike miles in sweltering conditions. When she couldn’t walk a foot further, Pentland detailed how she sat down, deciding she would be happy to die on the spot. When she refused to budge to get up, a male counselor smacked her hard across the face twice.

The abusive environments Pentland was placed in as a child led to her developing PTSD, something she only discovered as an adult when she began seeing a therapist. “I had never, as an adult, actively sought help for myself,” she writes. “I had been reluctant to do that because I had had so many bad experiences with therapy in my youth.”

But after describing how she felt an overwhelming sense of anxiety that sometimes led to panic attacks, the therapist diagnosed her with PTSD.

“I had been making jokes for years about having it, but I never let it sink in that I actually did,” Pentland admits. “It made sense, but also I felt ridiculous about it… But I guess it was time to admit that my experiences were not just funny anecdotes I’d collected. They were real and painful things that I’d lived through, and they were going to destroy me if I didn’t look at the fact that I had been victimized.”

“I don’t want to be called a victim because I don’t want to be called a survivor,” she adds. “I hate that. It implies that the suffering is over, and I know better. Don’t call me a survivor until I’m dead.”

Pentland hopes that by sharing her experience she can help raise awareness about the predatory and abusive behavior that often occurs in reform schools, like the ones she was sent to. “These places are still out there and I want it to stop,” she recently told People. “I don’t think about what I’ve lost anymore. I think about what other people are losing right now or what they’re going to lose if it doesn’t change.”


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