How Is Brett Goldstein as a Stand Up Comedian?

I had some serious reservations about Brett Goldstein as a stand-up comedian, reservations that the trailer for his special Second Best Night of Your Life did little to assuage. There’s something about Goldstein that feels fundamentally at odds with the demands of stand-up. Can a notoriously nice guy actually kill on stage while remaining a notoriously nice guy?

Mostly, yes. There’s nothing groundbreaking about his first HBO special, and not much that’s particularly insightful either, but Second Best Night is more than just the novelty of watching Roy Kent do stand-up. Goldstein is funny, charming, and affable, and his comedy feels like the kind of loose, tipsy conversation a Brit might have with an American friend at a pub after one too many beers.

A lot of his material leans on the well-worn differences between Britain and America, everything from the lack of privacy in American public restrooms to the jarring way Americans end phone calls. There’s also, of course, the obligatory bit about how Brits and Americans treat the C-word.

The story behind the special’s title is peak Brett Goldstein. The best day of his life, he says, was the day he appeared on Sesame Street, and he jokes that nothing else, not even having kids, will ever top hanging out with the Cookie Monster, whom he describes as an addict still in his “fun stage.”

Elsewhere, he cracks jokes about toxic masculinity, imagines how much better boxing would be if fighters took MDMA before matches, and roasts Shakespeare for his ridiculous plots while singing the praises of musicals.

His section on relationships and singledom gets the closest to something personal, but even then, Goldstein keeps his distance. He’s funny, but there’s no real vulnerability. Even his self-deprecation feels packaged, relying on broad stereotypes about men or Brits. It feels like he’s still figuring out his identity as a comedian, someone who isn’t quite ready to bleed a little on stage the way the greats often do. He mentions Ted Lasso and Sesame Street, but he never digs deeper, takes real risks, or even tries to subvert the format.

If he weren’t Brett Goldstein, I’m not sure HBO would have given him a microphone. He’s an A+ human being, but a B- comedian, which certainly makes Second Best Night of Your Life worthwhile but hardly necessary.