28. Judd Apatow & Adam Sandler

Adam Sandler is one of Hollywood’s well-established comedians. He has made a name for himself with his string of comedic movies back in the late 1990s. His iconic movies include Happy Gillmore, Billy Madison, Waterboy, and Big Daddy. In the 2000s, he further gained a lucrative degree of fame with his works in 50 First Dates, Click, and Anger Management. During Adam’s rise to fame, his profitable fate was intertwined with then-aspiring director Judd Apatow.

They were roommates and even had a hand in Happy Gilmore. He did some uncredited rewrites for the iconic Sandler movie. Moreover, he also helped produce some of Adam’s stand-up CDs. These eventually opened the gates to success for the director, and he would direct or produce critically acclaimed movies such as The 40-Year-Old Virgin, Knocked-Up, Superbad, and Forgetting Sarah Marshall. To his credit, Judd stood out with his unique brand of campy comedy that would quickly capture the hearts of many across the world and remains to be one of Hollywood’s best comedy directors.