At the 2026 Golden Globe Awards, host Nikki Glaser delivered a monologue that left one A-list nominee squirming in his seat. The target of her sharpest barbs was none other than Leonardo DiCaprio, whom she roasted for his well-documented history of dating women significantly younger than him.
The Awkward Monologue Moment
Glaser, who warned DiCaprio in advance about the joke, didn't hold back. Addressing the 51-year-old actor, who was nominated for Best Actor, she said, "What a career you've had, countless iconic performances, you've worked with every great director, you've won three Golden Globes, an Oscar and the most impressive thing is you were able to accomplish all of that before your girlfriend turned 30." The camera cut to DiCaprio offering an awkward smile and a thumbs-up from the audience.
The comedian later admitted the joke was "cheap" but defended it by stating there was little else about the notoriously private star to mock. "Leo, I'm sorry I made that joke … I tried not to but, you know, we don't know anything else about you, man. There's nothing else, open up," she quipped. DiCaprio's current romantic link is with 27-year-old Italian model Vittoria Ceretti.
The Deep Dive into a 1991 Teen Beat Interview
In her search for material, Glaser claimed the most in-depth profile she could find on the actor was a 1991 Teen Beat magazine questionnaire he completed as a teenage star on Growing Pains. She challenged viewers to look it up, proclaiming, "Look it up, that's real!"
The internet quickly obliged, with fans sharing screenshots of the handwritten Q&A across social media. The teenage DiCaprio listed:
- His first ambition: Acting
- First album bought: Michael Jackson's Thriller
- Favourite actor/actress: Jack Nicholson and Meg Ryan
- Dream car: A solar-powered Jaguar
- Favourite food: "Pasta, pasta and more pasta"
- Favourite music: Pink Floyd, Harry Connick Jr., and MC Hammer's "Can't Touch This"
Online reactions praised both DiCaprio's eclectic teenage tastes and Glaser's "investigative journalism."
Not the First Time: Jennifer Lawrence's Previous Jab
Glaser's roast was not the first recent public dig at DiCaprio's personal life. Just a month earlier, in December 2025, his Don't Look Up co-star Jennifer Lawrence appeared to deliver a subtle jab during a Variety "Actors on Actors" interview.
Discussing his role as a father in the film One Battle After Another, Lawrence said, "I'd really love seeing you to be a dad. I'm so sad that you don't have a teenage daughter. You look great with one." DiCaprio's puzzled reaction went viral, with fans on social media platform X calling it "sophisticated and perfectly delivered shade."
Navigating Life in the Spotlight
The article also touches on the challenges faced by those in DiCaprio's inner circle. In a 2025 interview with Vogue France, girlfriend Vittoria Ceretti spoke about the "extremely annoying" aspect of dating a global icon, noting how she became labelled as "'girlfriend of'" rather than being seen for herself.
For his part, DiCaprio has long maintained a philosophy of privacy. In a year-end conversation with TIME magazine, he stated, "I think my simple philosophy is only get out there and do something when you have something to say, or you have something to show for it. Otherwise, just disappear as much as you possibly can." A strategy that, as the Golden Globes proved, makes him a tantalizing target for comedians when he does emerge.
