No, this is not a picture of Dumbledore after he faked his death and ran away to the Caribbean because he was truly sick of all that Hogwarts drama. It’s also not a picture of a shrunken Randy Quaid shooting Vermont Public Access’ version of The Biggest Loser. It’s 68-year-old David Letterman using his millions to live that lavish retired life. David Letterman spent decades in a nipple-suffocating suit (I think he even wore it to bed), so he has freed himself of that Men’s Warehouse cocoon and is living it up in St. Barts.
Now, if I was a multi-multi-millionaire retiree like David Letterman, I’d be spending all of my days lounging on a pile of naked Prince Hot Ginge impersonators while smoking the finest of the finest good shit out of a Baccarat dick bong as Stacey Q and Martika performed Showgirls: The Musical live in front of me. But for some reason, David Letterman chose to go to St. Barts with his wife Regina Lasko. Weird, but it’s his millions and his life!
Letterman is also giving me “Santa Claus if Santa Claus was in the witness protection program” vibes and I’m into that, so yeah, I’d put on a butt-less elf onesie and hit it hard.