Photographer: Marius Bugge

Netflix’s Roast of Tom Brady was one of Hollywood’s biggest nights of the year, and comedian Sam Jay might have scored the biggest laugh of the evening with her burn of Patriots’ quarterback and Brady’s predecessor Drew Bledsoe. Because Bledsoe didn’t play one second of New England’s Super Bowl XXXVI victory, Sam (née Samaria Johnson)...

Big Jay Oakerson just might be the busiest man in showbiz. He’s a touring stand-up comic, and he appears on screens big and small: Big Jay was privy to JLo’s iconic stripper dance as a deejay in the movie Hustlers and has regularly riffed with comedy superstars on TV shows including Louie, Inside Amy Schumer...

Julia Scotti calls herself a female “of transgender experience,” which is to say that the woman used to be a man. And even though that man—Rick Scotti—was a comedian successful enough to tour with Chris Rock and Jerry Seinfeld and open for acts including Lou Rawls and Chicago, it wasn’t until he became she that...