It’s well past midnight when Yasiin Bey, also known as Mos Def, finally takes to the stage. The venue, a dark backroom in Dalston, is far more low key than the stadiums at which he has spent two decades performing and the crowd is considerably smaller than he is used to. But, for the first time, it is not hip-hop that brings Bey to the stage. “I always wanted to do standup but I got hijacked by rap,” he tells the crowd. “I feel free.”

The 41-year-old, who began his career in the public eye as a child actor, is one of the most respected and well-known hip-hop artists of the past two decades. Having formed rap duo Black Star in the mid-90s with Talib Kweli, he has since worked with everyone from De La Soul to Bobby Womack and Kanye West.

Yet, while he has dabbled in everything from acting to designing clothes, until now comedy was an unexplored avenue. The Saturday night show was Bey’s European debut of his standup show, and only the second time he has performed it in public, having given a version of the set its first public outing in Montreal in Canada two weeks ago.

The show, titled The Benny Trill Show, was in partnership with London’s NTS radio and referenced everything from Donald Trump and Bobby Shmurda to Banksy and even the migration crisis, with varying degrees of comic success.

It was also brought to an uncomfortable halt midway when Bey was discussing the recent transition of Caitlyn Jenner. Lines such as “some people get freaked out when you knew someone as a dude for all of your life and then suddenly they’re not a dude anymore … don’t be so hard on me that I’m just quite freaked out by that”, were met with a silent room and even prompted several audience members to walk out, with one calling on Bey to “stop being transphobic, it’s rude”.

Bey performed his standup fresh from an appearance at Banksy’s Weston-super-Mare ”bemusement” park, Dismaland, and wore a hoodie with the park’s logo for the show. “I went to Dismaland today,” he told the crowd. “And I’m happy to report that Banksy is a strong black woman.”

He also used the set to weigh in on the continuing dispute between rappers Drake and Meek Mill. “I don’t care about rap as much as I used to,” admitted Bey. “I love rap but I don’t care about it. It’s like a big WWF tournament, a bunch of arguing over-inflated egos. I felt the most bad for Nicki Minaj, who’s in the middle of this rapping skirmish between these two dudes. She’s a better rapper than both of them and she don’t even have no pants on when she raps. That’s confidence.”

He added: “They turned rap into the preferred drug of choice … if Donald Trump was black, he would be the personification of rap.”

Despite having established himself as an outspoken figure against everything from nuclear weapons to police brutality and the prejudice suffered by the black community in America, Bey’s set made only a passing illusion to his activism. “At least the police here aren’t trying to kill me,” he said.

It is not known where Bey plans to take his standup routine next and whether comedy will become a permanent part of his repertoire. However, he may have some way to go until his comedy takes him to the same venues that have played host to him at the peak of his hip-hop career.

“Seriously though, am I funny?” Bey asked the crowd towards the end of his hour-long set. Aside from a few tentatively raised hands, the room was otherwise silent.