Jimmy Fallon

Even from this prom photo alone, we could already tell that Jimmy Fallon was bound to be a funny guy. It would take the world of comedy a few years to truly appreciate his talents, though. He began pursuing a career in entertainment in his early 20s, landing a spot in the Saturday Night Live cast in 1998.

It was all uphill from there. His sketch comedy stint allowed him to break into film and later late-night hosting. These days, Fallon is wearing much better (and probably designer label) suits as he presents The Tonight Show. He also owns a $15 million New York penthouse, which he listed for sale in 2021.