Jimmy first got his big break in September 1998 when, after years of hoping, praying and perfecting his craft, he debuted on Saturday Night Live.
He told Rolling Stone that being on SNL was the dream of a lifetime:
"This was my ultimate goal. If I ever cut into a birthday cake and made a wish, I would wish to be on SNL. If I threw a coin into a fountain, I would wish to be on SNL. If I saw a shooting star, I would wish to be on SNL....
I had no other plan. I didn't have friends, I didn't have a girlfriend, I didn't have anything going on. I had my career, that was it."
His days on SNL and roles on successful feature films earned Jimmy the spot on The Tonight Show where he gets to spend time with millions of Americans every weeknight! Even though he may be rich and famous today, Jimmy will never forget where he came from...
That's why he shared a picture of his very own "Prom Fail" following a segment he did on the Tonight Show! Jimmy took to Twitter to release a prom picture so giggle-worthy, we have to laugh right along with him:
"My date didn't tell me she was getting a tan and high heels for the prom. Standing next to her I looked so pale and so small. #PromFail."
His prom picture is as funny as it is relatable! We've all had unflattering pictures snapped of us before a big school dance.