Judd Apatow has one of the most impressive comedy resumes of anyone, anywhere. His Apatow Productions has produced and developed the television series Freaks and Geeks, Undeclared, Girls, Love and Crashing, he has directed the hit movies The 40-Year-Old Virgin, Knocked Up, Funny People, This Is 40 and Trainwreck, and produced another dozen smash comedies on film since the late 1990s. Before that, he wrote and produced on The Ben Stiller Show and The Larry Sanders Show. Before that, he infamously interviewed famous comedians while still in high school in the mid 1980s. As he approaches 50, though, Apatow has returned to his comedy roots and filming his first stand-up comedy special for Netflix. which he’s recording at Just For Laughs in Montreal.

I sat down with him at The Olive Tree Cafe above The Comedy Cellar as he made his final preparations for it, so let’s get to it!