Apatow, in New York to promote his new Netflix comedy special as well as catch Springsteen's Broadway residency, told Jimmy Fallon, "I've only met him once before, which was in 1991, Garry Shandling hosted the Grammys and I was writing for him, and I said to Garry, 'We're taking a picture with Bruce Springsteen because you're the host and you're allowed to do that.'"
Apatow previously posted the photo with Springsteen on Instagram following Shandling's March 2016 death.
The Trainwreck director added that he was hopeful that the Broadway show would allow him to meet Springsteen again. "Well, if he wants to invite me backstage," he said.
The director reportedly wrote a cameo for Springsteen into his 2009 film Funny People as a voice of reason for Adam Sandler's character, but the role ultimately went to Eminem.
Speaking to Rolling Stone at the 2013 MusiCares Person of the Year gala for Springsteen, Apatow said of attempting to work with the E Street rocker. "I feel like I did once and failed, but I'll take another run at him. He did it for The Wrestler, he should do it for me."
On the Tonight Show, Apatow also talked about his four-hour documentary dedicated to Shandling's life, his cameo in James Franco's The Disaster Artist, where Apatow plays a caricaturized version of himself, as well as the Golden Globes' flawed classification of their Comedy category: