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30 Rock brought some unique characters to life, from quirky head writer Liz Lemon (Tina Fey) to polite and cheerful Kenneth Parcell (Jack McBrayer).

All seem to have their own way of standing out in the TV show, and writer Frank Rossitano (Judah Friedlander) is no exception. If you have watched 30 Rock, you would know Frank has a super laid back, slob look and wore thick frame eyeglasses.

However, what was most iconic about his wardrobe was his trucker hats. Whose choice was it to have this character in weird hats? Mental Floss pointed out that it was actually Judah Friedlander’s idea.

Frank Rossitano’s hats and Judah’s role on ’30 Rock’

Judah Friedlander as Frank Rossitano, Patti Lupone as Sylvia Rossitano
Judah Friedlander as Frank Rossitano, Patti Lupone as Sylvia Rossitano | Ali Goldstein/NBC

Frank Rossitano is a lead writer on TGS with Tracy Jordan. His character appears in just about every episode of 30 Rock. He is wearing a trucker hat in every appearance he makes, which adds up to 198 hats!

These hats are no ordinary trucker hats, and each one sports a different slogan or word. According to Friedlander’s 30 Rock Fandom page, he designed each one. Screen Rant rated the most iconic of Frank’s hats, naming the hat that simply says “why” as number one.

When Friedlander was cast for the role, he insisted on looking like himself and brought his own sense of style to the character. In an interview with Flavorwire, Friedlander explained the hats were solely his idea. He explained, “the character was not supposed to be wearing glasses or a hat. But you know, before doing 30 Rock, I’d done lots of movies, and in a lot of those I completely changed my appearance as well as the way I talked… so when I was doing this show, I told them, ‘I’ve gotta look like me’… my look is very particular to my stand up, and it’s all interconnected.”

In another interview with WABE, he also explained that he had to sign a six-year contract before starting the show. Since he had to commit to something long term, he wanted to look like he does every day.

Friedlander also pointed out that he had more of a say in the first and second seasons. However, as the show progressed, the writing became more detailed, and there was not a lot of room for improvisation. 

Judah Friedlander’s career

Judah Friedlander started his career in show business as a soundman on Chris Rock’s short Who is Chris Rock? Eventually, Friedlander began acting and had appearances in Wet Hot American SummerMeet the Parents, and Zoolander.

His big debut and most notable role came in 2003 when he portrayed Toby Radloff in American Splendor. 

What Judah is up to now

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When 30 Rock ended in 2013, Friedlander continued to make appearances in movies and television shows, like Unbreakable Kimmy Schmidt. He voiced characters on American Dad and Bob’s Burgers.

In 2015, Netflix created a prequel to Wet Hot American Summer, and Friedlander was able to revive his role as Ron von Kleinstein. Throughout his acting career, Friedlander has also maintained a stand-up comedy career. He headlines at various stand-up comedy clubs in New York and Los Angeles.

In 2019, Friedlander went on a stand-up tour called “Future President.” When it comes to his stand up performances, Friedlander likes to keep things intimate by performing at smaller venues. He also enjoys talking to the crowd while doing his comedy act.

This past year, Friedlander started a virtual tour titled “The World Champ Tour.”