Cameo Crazy: Stars Playing Themselves On Screen

As Adam Sandler films have taught us time and time again, a good cameo can be extremely funny, especially when a cheesy pop culture icon plays him or herself. Sandler’s latest, “That’s My Boy,” drives home this lesson (in a 5.0 Mustang) with a fantastic cameo by early ’90s rapper/late ’90s joke, Vanilla Ice. It’s a hilarious role, no doubt, but it got me wondering: Am I laughing with Ice, or laughing at him? And while I was pondering this sage ... more 

As Adam Sandler films have taught us time and time again, a good cameo can be extremely funny, especially when a cheesy pop culture icon plays him or herself. Sandler’s latest, “That’s My Boy,” drives home this lesson (in a 5.0 Mustang) with a fantastic cameo by early ’90s rapper/late ’90s joke, Vanilla Ice. It’s a hilarious role, no doubt, but it got me wondering: Am I laughing with Ice, or laughing at him? And while I was pondering this sage line of questioning, I figured I might as well ask the same thing about a collection of my favorite comedic cameos. 

By Adam Pockross less