10 Best Celebrity Cameos In How I Met Your Mother
2. Kyle MacLachan
When Ted gets together with Zoey, he also wrecks her marriage with eccentric millionaire George Van Smoot, aka The Captain, played by Kyle MacLachlan. Though most of MacLachlan's filmography is more dramatic, David Lynch style films and shows, he shows off some serious comedic chops in the role.
The Captain's half friendly/half creepy demeanor makes him a standout, with his boat obsession as hilarious as it is oddly specific. He appears in a few episodes in Season 6 for a one sided friendship with Ted, before returning for the final two seasons as Lily's new boss.
The Captain's sheer weirdness shows how great the later seasons of How I Met Your Mother can be. In the hands of a less skilled actor, he wouldn't have been nearly as funny.