Iron Man (2008)

Towards the early half of the film Stan makes his first appearance in the Marvel Cinematic Universe at an event that Tony Stark is attending. Tony walks up behind a man in a robe and taps him on the back and says “You look great, Heff” as he walks by. The man turns around and it happens to be Stan, whom Stark has mistaken for Hugh Hefner It’s a hilarious moment that is a great way to start off Stan’s adventures into the MCU.