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Her Grandfather Is a Conservative Icon. Her Comedy Is Liberal AF

How Rosebud Baker upended her blue-blood roots to become one of today’s edgiest stand-ups

Rosebud Baker at the 2019 Clusterfest "Roast Battle" in San Francisco

Jeff Kravitz/FilmMagic/Getty Images

It’s hard to imagine a more outlandish origin story than Rosebud Baker’s accidental debut as a stand-up comedian. It happened during a White House dinner and, as Baker recalls, it was a disaster. The granddaughter of Secretary of State James Addison Baker III, she was barely seven years old when her parents stood her on a chair so she could charm the assembled VIPs, including the then-president, George H.W. Bush, with a cute-as-a-button oration.

“I remember trying to congratulate the president for something and calling him by his first name,” Baker says while nursing a half-and-half-infused cup of joe at a jam-packed coffee emporium in Manhattan’s Gramercy Park neighborhood. She is blonde, pretty, and five-foot-three, but possessed of a brawny voice (deepened no doubt by constant vaping) and a magnetic intensity that belie her petite frame. 

“It was this big dinner. And I remember being like, ‘George!’” she says. “I got this huge laugh. And I found it so embarrassing. The feeling of getting a laugh without knowing why, I was like, ‘This is humiliating, I never want to come back here, I’ve embarrassed myself, I don’t belong here.’

“But now,” she adds, “I love it.”

Three decades later — with the benefit of life experiences more typical of comedian biographies, such as family dysfunction, alcoholism, explosive rage, years of therapy, and profound grief, not necessarily in that order — Baker is coming into her own as a gifted writer and performer whose dark, close-to-the-bone comic sensibility is tickling audiences and peers alike.

“The first time I saw Rosebud Baker was onstage at [the New York comedy club] The Stand. And within the first 15 seconds, I was like, ‘Who is this?’” says comedy superstar Bill Burr, whose podcast network, All Things Comedy, hosts Baker’s “Devil’s Advocate” show and recently co-produced her breakout special, “Whiskey Fists,” for Comedy Central’s YouTube Channel. (The latter title is an homage of sorts to a long-ago ex-boyfriend, a physically abusive drunk who was often so inebriated during his attempts to beat her up that his punches didn’t land.) “I loved her fearlessness, the self-deprecation, the vulnerability. As an old comic, I always get excited when I see someone new that I know is going to be great.”

Ditto comedian and talk-radio jock Jim Norton: “She’s very dark, and I like darker comedians. I like people who are not afraid to tell a punchline that might make the audience sad while still being legitimately funny.”

Baker’s comedic persona — honed over the past eight years since she first stepped in front of an open mic at a comedy club outside Austin, in the middle of what she describes as a Thelma & Louise cross-country trip with a childhood friend — ranges from merciless self-excavation to slashing social satire, graced by intelligence and nuance. It’s punctuated by a self-aware chuckle that somehow makes her likable even when she’s at her most challenging and offensive. 

Her jokes frequently feature a sinister twist, as when she waylays a premise that Jerry Seinfeld might have been comfortable with — say, the moral superiority of dogs to cats — by recounting how she had to euthanize her dog a year after putting down her cat: “I would have snapped my cat’s neck to save my dog. And if you’re a cat person and think I’m a monster, just know I would have snapped your cat’s neck to save my dog.”

Lampooning white people’s propensity for cultural thievery, she recounts a conversation with a Puerto Rican friend who complained about white women wearing hoop earrings: “I was like, ‘Cool. I get it. Your people came up with this shit. But if you want me to get my own identity, my people came up with appropriation.’” 

About an ex-boyfriend she was desperate to marry, Baker moves seamlessly from raunchy to diabolical: ‘I was just jerking him off like I was banging on a vending machine trying to shake a ring out…To be honest, I should have blown him more. That’s what my grandma says. She’s a huge whore, my grandma. I’m just kidding, she’s dead.”

She also doesn’t avoid mocking her illustrious upbringing, crafting jokes about the first time she brought a Black boyfriend home to meet her ultraconservative dad, and about her complicated relationship with being a liberal: “I feel like a hypocrite …  Because my sisters will be online, and they’re like, ‘If you don’t vote, you’re being complicit.’ And I’m like, ‘Yeah that’s true, but Saudi oil money put us through college.’”

Baker grew up the eldest of five sisters in Alexandria, Virginia, and later nearby McLean, both gilded suburbs of Washington, D.C., in the third-wealthiest county in the United States. Her famous and powerful grandfather was the president’s best friend, so Rosebud — who was born “Rosemary” but nicknamed “Bud” due to her tomboy ways, such as refusing to wear dresses or fancy shoes (“I still wear formal clothes like a toddler who’s been forced to dress up for church”) — was continually thrown together with the Bush grandkids, who were accompanied by a Secret Service detail that took up sentry duty in the Baker family home.

“When people ask me ‘What was that like?’ I’m like, ‘Well, it just was what it was,’ ” Baker says. “I didn’t think of it as anything special. We would go to the White House and I was told it was a special thing. But because it wasn’t separate from who we were as a family, it didn’t really knock my socks off. I remember being a kid in the White House and being, like, ‘Wait. So the president has a rental? This isn’t even his?’ ”

She recalls that her dad James “Jamie” Baker IV — a recently retired senior partner at the Washington offices of Baker, Botts, the massive Houston-based law firm built by her great-great-great grandfather in 1872 — was a largely absent workaholic. His emotional distance was the result of growing up in a family that valued competitiveness and accomplishment above all as the currency of love. Needless to say, there was zero precedent for stand-up comedy in two centuries of Baker family history. 

“I did try for a long time to keep it hidden from them, just because I didn’t want their input,” says Rosebud, who recently searched New York Times reporter Peter Baker’s (no relation) magisterial biography of her granddad, “The Man Who Ran Washington,” for clues to her father’s psyche and the astringent family dynamic. “Because it’s a precious thing, and your family will fuck up anything that’s precious to you. I tried to keep them as far away from it as possible for a long time, with the exception of my sisters, who I’m really close to. But now they’ve all kind of seen it, I’m assuming, and I’ve gotten mixed reviews. Generally speaking they love it — until they hear something they don’t like. And then it’s not comedy anymore, I’m just saying blasphemous things.

“But if they don’t like it, I couldn’t care less, honestly,” she adds. “If a painter makes a shitty painting, their family doesn’t call them up and say, ‘We didn’t raise you to be this much of a piece of shit.’ My family won’t say it like that. They’ll just say things like ‘That was inappropriate,’ ‘That’s selfish of you,’ ‘I can’t believe you would tarnish the memory of so-and-so’ or whatever.”

As for James Baker III, the 91-year-old former secretary of state known as “The Chief” among his progeny? He has not lost his touch for either politics or diplomacy. “Bud is the first of our 19 grandchildren,” he says by email regarding his irreverent granddaughter, “and we love her very much, just as we do each and every one of the others.”

Rosebud’s mother Nancy, the Texas-born daughter of a Connecticut insurance executive, is a talented landscape, portrait, and still-life painter, but struggled with the alcoholism that ran through her kinfolk. Rosebud recalls an afternoon growing up when her mom — who has been sober for many years and these days lives in Maine — got into a car accident and was hauled off to jail in a police car after attempting while intoxicated to ferry her middle-school-age daughter to ballet class. Rosebud herself suffered from an eating disorder as a kid, unable to stop obsessing over the food that she’d hidden under her bed, relishing the moment when she could leave her school friends to consume it alone in secret.

 “I’ve always had a drug addict’s mindset,” she says. “I’m always looking for the next thrill” — although she says she’s now able to “talk down” that self-destructive impulse.    

Early on, she demonstrated an aptitude for performing, writing skits, and marshaling neighborhood kids to stage them. “She has always been hysterically funny,” says her six-years-younger sister Mary Stuart Baker, an editor in the digital media department of a New York art gallery. “She’s always been the person in our family who, when things were uncomfortable, which they often were, she would make a joke about it. To be brought up in a WASP family, that’s something that not everybody gets, but I think that’s largely the reason me and my sisters are as well-adjusted as we are — that we had someone there, growing up, to point out the ridiculousness of what was playing out in front of us.”

At Langley High School, Rosebud excelled mainly at rebelling against authority figures. She was suspended from the cheerleading squad and received, by her own account, lousy grades. And by the time she graduated, her parents’ marriage was in ruins.

Then a freak accident at a backyard graduation party, on June 15, 2002, shattered the family forever. Rosebud’s seven-year-old sister, Graeme, drowned in a hot tub, sucked underwater by a powerful drain while several adults, including Nancy, tried in vain to free her. Rosebud had dropped off her kid sister, a twin, at the party, and departed for what she hoped would be a better party, when she was suddenly summoned home with the vague explanation that “something’s happened.” The tragedy ended up escalating Rosebud’s burgeoning drinking problem.

“I can’t speak for everyone else, because grief is a lot like Covid in terms of how it’s experienced,” she tells me. “But for me, it felt science-fictiony, like getting very old very quickly. I woke up one day and before I went to bed, I had lost my understanding of people, relationships, and reality. When you’re a teenager you have a feeling of being invincible, you think your family will always be there and certain things will never change. Generally speaking those assumptions tend to fade over time. I just lost them, let’s say… more efficiently? Does that sound optimistic or cold blooded? I’m always mixing those up.”

In the years that followed, everything reached “a fever pitch,” Baker says. She self-medicated with mass quantities of liquor. At Boston’s Emerson College (whose famous alumni include, among many others, Jay Leno and Bill Burr), she majored in acting — and minored, it seemed, in blackout drunkenness, one-night stands,  suicidal ideation, and blind rage that occasionally manifested itself in drawing blood from whichever boyfriend she had just socked in the face.

“The grief was so overwhelming and I didn’t have the tools to know that you could just feel your grief, and that it would pass, and that it would be OK,” she says. “The drinking, my sister’s death, leaving for college and being on my own — all of that combined to create this perfect storm.”

Following the time-honored WASP playbook, her family suppressed their grief in the wake of Graeme’s death and pretended that life could go on as usual. “You can’t put grief in the middle of a country club, you know? It doesn’t belong there,” Rosebud noted during a recent installment of Marc Maron’s WTF podcast.  She recalled that much to the Baker girls’ shock, their father showed up at their sister’s funeral with a new woman on his arm.

Yet Rosebud credits her dad for, among other things, pointing out that she was genuinely hilarious and encouraging her to pursue stand-up comedy instead of her initial, even dicier, career choice of acting, which had required her to make ends meet by working as a nanny and a waitress, and, much later, taking a gig writing horoscopes (as “Rosey Baker”) for the Elite Daily website. “I definitely inherited my sense of humor from him,” she says. “Also, he is the person in my family I have the most contentious relationship with, and if your humor is dry and biting and sarcastic, you’re gonna draw inspiration from the people who get that out of you.” 

After graduating from college with a B.A. in acting, Rosebud and the sister closest to her in age, Hallie, these days a pediatric nurse, went on a grand tour of Europe, which Rosebud spent in an alcoholic haze. “The time that I spent in Europe is pretty much a blackout,” she tells me. “It was supposed to be a trip that my sister had planned for the two of us, but it had gotten to a point with my drinking where she was, like, ‘I’m getting out of here.’ And she left.”

Rosebud stayed on, “but it was just an exercise in futility,” she recalls, and when her family stopped wiring money, she agreed to come home and enter a rehab facility. But instead of returning to Washington, as her plane ticket indicated, she got off at JFK and took a cab to Brooklyn, where a then-boyfriend was living with a heavy metal band across the street from a sewage plant. Rosebud moved in.

She eventually joined group therapy, although she lied lavishly during those sessions, even to the point of claiming to have four living sisters. She finally took it seriously after finding a shrink she trusted in Brooklyn who helped her confront and process her grief. (Baker is now able to joke onstage about her dead sister, telling audiences that Graeme is the sister she gets along with best: “She’s a good listener.”) With the help of AA meetings, meanwhile, she can credit herself with more than 14 years of sobriety.  

“At some point,” she says, “the adult took over and I’ve learned how to kind of parent myself.” She added that watching her mom get sober after her DUI “was a major influence on how I ended up getting clean myself. She never pushed me to quit drinking, but she was the first person I told after I got through a week without drinking. Seeing how much better her life became and how authentically she started living it, I wanted that for myself. She just became so comfortable in her own skin as this zany, joyful, artistic weirdo. I loved it.”

In retrospect, Baker’s journey to the comedy world seems inevitable. Though she had been working sporadically as an actor — Off-Broadway, in independent films, and at one point appearing on a Sundance Channel reality series titled “Girls Who Like Boys Who Like Boys” — she felt most at home in New York’s comedy clubs where a number of stand-up comics had become her pals. Indeed, she had even begun trying her hand at writing — not jokes, exactly, but “funny ideas.”

During that cross-country drive with her friend eight years ago,  they had been listening nonstop to comedy routines on Pandora. When the open-mic opportunity presented itself as they passed through Austin, Rosebud was game.

“I decided to try it, and I think I got, like, one laugh and just got the fuck off the stage,” she recalls. “I didn’t get greedy. But I needed to do well and know that I had the courage to do it.” 

When she returned to New York, Baker ventured onstage at the Metropolitan Room in Manhattan’s Chelsea neighborhood, got a few more laughs, and quickly became an open-mic regular, doing as many as three spots a night at various clubs around the city. (On her way to her first open mic in New York, she tried to calm her nerves by walking all the way downtown from her Upper East Side nanny job to Chelsea, and took it as a good omen that she crossed paths with Joan Rivers and exchanged hellos with her as the comedy icon was getting into a cab.)

“I had no idea how to write a joke, even after about six months of doing open mics,” she says. “So I thought, I gotta learn how to write a joke. So I watched people’s specials” — Dave Attell, Amy Schumer, Dave Chapelle — “and transcribed the jokes by pressing the pause button after the setup, writing it down, and then pressing play, and writing down the punchline. And I was literally showing myself the anatomy of a joke.”  

Baker’s husband of 15 months, fellow stand-up comedian Andy Haynes, notes that her achievements can be traced back directly to her steely determination and intimidating work ethic. “Rosebud has just been able to know what she’s wanted to do and stay focused, and it’s pretty impressive,” says Haynes, who proposed in early 2020 as they quarantined together during the height of the Covid pandemic in a borrowed house in East Los Angeles. They were married in Washington Square Park in September 2020 and live in Manhattan.

“She works so hard, and she doesn’t seem to have any other concerns as far as her own well-being,” says Haynes, who, like his wife, is a recovering alcoholic. “I’ve seen her come back from being on tour after a week of writing, and she’s like, ‘Oh, I have four spots tonight,’ and I’m like, ‘You got four hours of sleep last night.’ But for her, it’s a non-negotiable. And I’m like, ‘All right, go to your four spots, psycho!’ ” 

Since early last year, Haynes and Baker have been appearing together in “Find Your Beach,” their twice-a-week podcast in which they laugh, bicker, make fun of each other and, usually with a smile, point out each other’s character flaws. Sometimes it gets very raw.

“It’s probably been a little bit of our marriage counseling and also our catharsis,” says Haynes. “We like to air our grievances and take it to the court of popular opinion. But it’s also kind of our love language. We like to roast each other.”

Haynes says that out of around 250 episodes so far — half available for free and half for paying Patreon subscribers — they have only had to scrap one because it wasn’t fit for public consumption. “We got in a real fight on it,” he explains.

Baker’s career — not only as a comedian, but as a writer and actress — has been hitting its stride in the past few years. Her performances have been featured regularly by Comedy Central, she wrote jokes for the channel’s Roast of Alec Baldwin, she had a star turn in the Amazon documentary series Inside Jokes about young stand-ups competing in Montreal’s prestigious Just For Laughs comedy festival (in which she was named a “New Face” of comedy), and this year she has been toiling in the writer’s room for the HBO Max sketch series That Damn Michael Che. Baker also joined the cast of the upcoming Hulu series Life & Beth, starring Michael Cera and Amy Schumer (who has been a close friend and comedy mentor).

“Something that popped for me with Rosebud is, I think it’s pretty rare to come on our radar as someone fully formed in their voice,” says Ryan Moran, Comedy Central’s senior talent and development executive. “She’s wildly comfortable onstage, and she’s comfortable making people uncomfortable. The first time I saw her do stand-up, she was making incredibly dark, sad, tragic topics so funny and relatable. It’s a very high degree of difficulty. The tightrope that she walks is so impressive, and that’s the thing that really drew us to her. It was just very obvious that she was going to go somewhere super special.”

Moran predicts that Baker is “going to be a huge stand-up comedian. She also has got such life experience that she has a narrative scripted television show in her, and I know she’s working on stuff. She’s going to be one of those people who’s got books and movies and TV shows. She’s next.”

But even if that were not the case, it wouldn’t have stopped Baker from chasing her dream. 

“The first five years that I was in comedy, no one knew anything about what I was doing,” she says. “I was just doing it because I loved it. It made me so happy, and I just thought, well, I’ll just keep doing this, because it makes me happy.”

From Rolling Stone US