Please Don't Destroy - Skydiving

John and Martin, nervously preparing for their first skydive, meet their tandem instructors — Ben and a man played by host Michael Keaton. During the pre-jump briefing, both instructors casually drop increasingly disturbing personal revelations (legal troubles, losing custody of his kids), leaving John and Martin horrified but strapped in with no way out. A background gag shows the plane's pilot watching a TikTok "How to Fly" tutorial on his phone mid-flight, adding a final absurdist layer to the mounting danger.

This was the first Please Don't Destroy segment of Season 50. The pilot background gag (watching a "How to Fly" TikTok video) was noted by many viewers as a highlight. Michael Keaton's delivery of the custody line was praised as a standout comedic moment. The sketch reached ~2.46M YouTube views as of research date.