From season 6 of 30 rock, Steve Buscemi as Lenny Wozniak going undercover in a high school, for reasons I can’t remember It’s episode 8, titled “The Tuxedo Begins.” These screen grabs come from multiple sources. Another picture after the jump that an excellent addition, he’s not just carrying one skateboard. 30 Rock has showed skateboards a couple times over the years and mentioned Tony Hawk at least once.