Judd Apatow was once a young, comedy-obsessed boy. As a teenager, he would interview famous comedians for his high school's radio station. But before that he wrote Steve Martin a letter and Steve Martin wrote back with a very personal response. This isn't just some form letter; Martin references Judd twice by name. Surprisingly, he also acknowledges in writing that he once took a young boy to Brazil, just for the afternoon, just to look at "girls!" Read the full letter below and try to imagine the amount of geeking out that resulted from it.
Woody Allen has done a pretty good job writing films, books, plays, and jokes but they're nothing compared to his letter. OK, those works are great but read some of these letters he writes Diane Keaton:
From 1969, around when they performed together in Play it Again, Sam:
Humans are clean slates. There are no qualities indigenous to men or women. True, there is a different biology, but all defining choices in life affect both sexes & a woman, any woman is capable of defining herself with total FREEDOM. Therefore women are anything they choose to be & frequently have chosen & defined themselves greater than men. [...]
Three months before he died of pancreatic cancer, Bill Hicks wrote this letter to The New Yorker's John Lahr to thank him for an article he'd written on Hicks. (The article is a pretty fantastic read as well. I'm definitely gonna start calling the television "Lucifer’s Dream Box.") In his letter, he talks about how following the article, creative possibilities feel "limitless" and says that "the offers finally match my long-held and deeply cherished creative aspirations." Fair warning, you'll probably get a tightening feeling behind your nose while reading this, and then a sour feeling in your jaw, and an itchy feeling in your eyes, and then [...]
Here's a letter that Phil Hartman wrote to an aspiring comedian who had sent him a tape of his work in 1997. In case you were ever wondering if Phil Hartman was a good guy, well, try to think of who else would not only respond to a letter/tape like this, but would listen to it and sent back a multi-page hand-written note with specific feedback and well wishes. This was when Phil was at the peak of his career, doing Newsradio, The Simpsons and a slew of other projects, so it's not like he wasn't busy. One of the all-time greatest, and gone far, far too soon.
Dear [Friend Name],
Hey, [Buddy/Dude/You]. I know we haven’t seen much of each other since you began working on [Show Name], and [Bar Show Formerly Produced Together] hasn’t been doing too great, but I wanted to let you know how proud I am of you.
When you and I both auditioned for [Show Name], who could have known who they would have picked? Maybe you? Maybe me? It was up in the air, and the choice must have been very difficult for [Casting Director Name] who called up both of our managers and asked to see us both on the same showcase because of our comparable talent. We both [...]