Nobody saw it coming. When Comedy Central announced the lineup for the 2015 Roast of Justin Bieber, the names were pretty standard. You had Kevin Hart, Snoop Dogg, Shaq, and the usual "Roast Master" Jeff Ross. Then, tucked in the press release like a strange garnish, was Martha Stewart.
People were confused. Why was the queen of suburban domesticity, the woman who literally wrote the book on "Good Things," sitting on a stage with Ludacris and a guy who calls himself the "Roastmaster General"? It felt like a glitch in the matrix.
But then she spoke.
In six minutes, Martha didn’t just participate; she committed a televised homicide. She wasn't just "funny for an old lady." She was the meanest, sharpest, and most calculated person on that stage. Even now, over a decade later, her set is widely considered the gold standard for how a non-comedian should handle a roast.
The Set That Changed Everything
Most people expected Martha to lean into the "sweet grandma" trope. You know, make a few jokes about cookies and then sit down politely. Instead, she walked up to the mic and immediately took aim at Kevin Hart’s height and bank account.
"Sitting and listening to you yell your jokes over the last hour is the hardest time I've ever done," she deadpanned.
The audience lost it. It was the perfect opening. By acknowledging her own 2004 prison sentence—the "elephant in the room" that she had spent years trying to move past—she signaled to everyone that she was playing for keeps. She wasn’t there to be a punchline; she was there to deliver them.
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Why the Prison Jokes Landed So Hard
The highlight of the Martha Stewart roast of Justin Bieber was, without a doubt, the "prison tips." At the time, Bieber was in the middle of his "bad boy" phase—peeing in buckets, drag racing in Miami, and generally being a public nuisance.
Martha looked him dead in the eye and told him he wouldn't last a week in lockup.
"The first thing you’ll need is a shank. I made mine out of a pin-tail comb and a pack of gum. It’s so simple. I found Bubbalicious works best, and it’s so much fun to say."
The contrast was peak comedy. Here is a woman who can tell you the exact thread count of a luxury duvet, describing how she "stuck" the biggest person in the chow hall to earn respect. It was absurdity at its finest. Honestly, the way she compared prison life to making "blueberry scones" is a writing masterclass. It took her public "shame" and turned it into a badge of "OG" status.
The Bromance Born in the Fire: Martha and Snoop
If you ever wonder why Martha Stewart and Snoop Dogg are best friends today, look no further than this roast. While the world remembers the jokes, the real legacy was the chemistry between the domestic diva and the West Coast rap legend.
Before the show even started, things were getting interesting. Martha has since admitted in interviews that she got a "contact high" from sitting next to Snoop for four hours while he smoked.
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"I inhaled a lot of Snoop's smoke," she told Jimmy Fallon later. "I was totally high by the time I got to the podium."
Whether it was the second-hand smoke or just a shared appreciation for the hustle, that night birthed one of the most iconic duos in pop culture history. It led directly to their show, Martha & Snoop’s Potluck Dinner Party, and a decade of Super Bowl commercials and joint business ventures. Without the Bieber roast, we probably don't get Martha Stewart appearing in Skechers ads with Snoop.
What Most People Get Wrong About Her Set
There’s a common misconception that Martha just read lines someone else wrote and had no idea what she was saying. While roasts always have a writing room (led by guys like Jesse Joyce and Tony Hinchcliffe), Martha wasn't a puppet.
She reportedly spent weeks practicing her delivery. She knew the rhythm. She understood that for a roast to work, the "mean" has to be balanced with a specific kind of "alpha" energy.
Take her joke about Ludacris, for example. She criticized his "parenting" (he has multiple children with different women) and then pivoted to a pitch for her own brand: "May I suggest pulling out sometime and finishing on some fine, highly absorbent Martha Stewart bed linens?"
It’s vulgar. It’s biting. And it’s a brilliant bit of brand placement. She was basically saying, "I'm a billionaire, I've been to jail, and I'm funnier than you. Buy my sheets."
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The Cultural Impact
The Martha Stewart roast of Justin Bieber did something very specific for Bieber, too. At the time, his brand was in the trash. He was the most hated teenager on the planet. By sitting there and taking those hits—especially from someone as "respectable" as Martha—he humanized himself.
It was a ritual of humiliation that allowed him to transition into his Purpose era. It basically gave the public permission to stop hating him for five minutes.
How to Roast Like Martha (Actionable Takeaways)
If you're ever in a position where you have to give a speech or a light-hearted roast, there are three things Martha did that you should steal:
- Own Your Baggage: She didn't wait for others to make prison jokes. She made them first, and she made them better. If you have an obvious flaw, lean into it.
- The Power of the Deadpan: Martha never laughed at her own jokes. She stayed "in character" as the stern, perfectionist mogul. The more serious you look while saying something ridiculous, the funnier it is.
- Know Your Audience: She didn't try to use slang or "act young." She used her own vocabulary—words like "diversification" and "regimen"—to insult people. It made the "street" jokes even more jarring and hilarious.
At 73 years old (at the time), Martha Stewart walked into a room full of young comics and rappers and walked out as the undisputed MVP. She proved that being a "lady" and being a "savage" aren't mutually exclusive.
If you haven't seen the clip in a while, go find it. It’s a reminder that sometimes the best "good thing" is a perfectly timed insult.
Next Steps for the Ultimate Roast Experience:
Check out the full unedited version of the roast on Paramount+ or Comedy Central’s digital archives. Pay close attention to the reaction shots of Shaq and Snoop during Martha's set; their genuine shock is half the fun. If you're interested in how the "unlikely duo" evolved, watch the first season of Martha & Snoop's Potluck Dinner Party to see how they turned that roast chemistry into a literal business empire.