Russell Brand and Sean “Diddy” Combs are both behind bars, but a 2009 YouTube video has put their old “straight guy date” back in the spotlight.
The clip, pulled from Brand’s since-defunct YouTube channel, shows the “Get Him to the Greek” co-stars flying private to Las Vegas in August 2009, trading crude jokes about their mission in Sin City. Combs, 57, draped his arm around Brand, 51, and declared him his “new best friend,” adding that they were “very, very, very dear friend[s]” who went “way back.”
Brand fired back with mock street cred, telling the camera, “We got a lot of history from the projects, of course. Very rough in those days.”
When Combs removed his arm, Brand quipped, “I liked it,” prompting Combs to ask, “Yeah, you liked it?” Brand then clarified, “I mean, I didn’t let it cross over into the area of being physically aroused or anything.” Combs shot back that there would be “none of that,” before explaining that the pair were “going on a straight guy date.”
Brand pressed the joke further, asking, “With a normal date … the best possible result of that date is sex. Now, with our heterosexual date, what is the best thing that could happen?”
Combs responded without hesitation, “We could find some women to have sex with.”
“That is our conclusion,” Brand said with a smile.
The video capped with Combs addressing the camera directly, promising, “You’re seeing us at the beginning of the 48 hours. As you know, what happens in Vegas, stays in Vegas. But we … really plan on going to the hospital.”
The Vegas trip came one month before Brand began dating Katy Perry. The couple married in October 2010 and split 14 months later when Brand filed for divorce in December 2011. At the time of the flight, Combs was in an on-and-off relationship with singer Cassie Ventura that would stretch until their final breakup in 2018.
Brand later reflected on the weekend during a May 2010 interview with Blacktree TV, calling it his “enforced holiday” with the Grammy winner. “He looked after me,” Brand said of Combs, describing him as “a very intense man” who is “very influential” and difficult to say no to.
The 2009 footage has gained fresh relevance as both men now serve prison sentences. On Monday, Brand received 10 years and six months at London’s HMP Wandsworth for one count of rape and three counts of sexual assault, charges he had denied and pleaded not guilty against. The facility has drawn scrutiny for overcrowding, vermin, violence among inmates and other inhumane conditions.
Combs, meanwhile, was convicted last July on two counts of transportation for prostitution and sentenced to 50 months. He was recently moved from FCI Fort Dix in New Jersey to FCI Allenwood Low in Pennsylvania following a hospital visit for a head injury. His scheduled release date is February 6, 2028.
Both men had built careers on bold public personas before their legal downfalls. Brand transitioned from stand-up comedy to Hollywood films and political commentary, while Combs built a hip-hop empire spanning music, fashion and spirits. Their 2009 collaboration on “Get Him to the Greek” — a spinoff of Brand’s breakout role in “Forgetting Sarah Marshall” — positioned them as unlikely comedy partners, with the YouTube video offering a behind-the-scenes glimpse of their off-screen dynamic.
The resurfaced clip has circulated widely as each man’s past behavior faces renewed scrutiny. Their casual banter about soliciting women, once presented as edgy humor, now lands differently given their subsequent convictions for sexual crimes.
Combs’ current release date is February 6, 2028.
