One of 30 Rock's innumerable running gags was the parade of unique hats worn by the fan-favorite character Frank Rossitano. While TSG staff Frank is not in every episode, the ones he's in do tend to feature a different hat each time.
Some are more iconic than others. This can be because of repetition (considering Frank is known to occasionally reuse a hat) or incorporation. While it didn't happen often, when one of his hats would be incorporated into the plot, it always proved humorous.
Kung Fu Beech - Season 1, Episode 8
"Kung Fu Beech" combines two traits common to the best Frank Rossitano hats. The first is a misspelling, which was done to varying degrees of success. The second: quirk.
The more bizarre the Frank Rossitano hat, the more memorable he becomes to the viewer. They are somehow a perfect glimpse into his personality before he even utters a line. The fact that the hats all came from Frank actor Judah Friedlander, according to his interview with Flavorwire, himself makes that even more true.
Crop Octagon - Season 3, Episode 20
"Crop Octagon" is arguably the biggest question mark amongst the stable of Frank Rossitano hats. Does it have to do with the difficulty of cropping an image into the shape of an octagon? Is it some sort of reference to an MMA fight in a cornfield?
The best thing about Frank's hats is how they frequently go entirely unmentioned. His coworkers accept him and his hats, quirks and all. "Crop Octagon" is never explained because "Crop Octagon" requires no explanation.
Ninja Expert - Season 1, Episode 1
The first is one of the best. "Ninja Expert" is a terrific first foray into Frank's personality. He's a nerd and a goofball. Furthermore, Frank knows that he's a nerd and a goofball. Lastly, Frank likes that he's a nerd and a goofball.
Frank's first hat lets the audience know that they're in for a unique character they won't soon forget. That Frank continues informing the audience of this throughout seven seasons is the key to his appeal.
Speling Expirt - Season 2, Episode 14
"Speling Expirt" is a hat very much in line with the audience's vibe of Frank Rossitano. It's the snark in his personality, his utter disregard of social conventions. Frank Rossitano's brand of humor frequently strays into the overtly ironic, so this hat serves as a companion piece.
"Speling Expirt" is perfectly on-brand for Frank because he's consistently trying to make those around him laugh. He's not hungry for attention; it's just what he thrives on.
Half Centaur - Season 2, Episode 5
30 Rock is so easy to watch because it's wholly unique. Outside of Saturday Night Live, which is effectively 30 Rock's source material, 30 Rock is in a comedic class all their own.
Frank is arguably the best example of 30 Rock's unique brand of humor. There really is no better hat than "Half Centaur" to tell the audience just how funny the man is. When a hat can make a Greek mythology joke indicative of a personality, it's comedic gold.
Ammnesia - Season 7, Episode 3
This late addition to the series is probably Frank's last great hat. "Ammnesia" is one of those hats that pokes fun at itself and, arguably, the wearer himself. Frank walks around all day wearing a hat that says "Ammnesia" so the people around him will think one of several things.
The first is that it's a misspelling. The second is that he doesn't know how to spell "amnesia." The third is that he's forgotten how to spell "amnesia." The viewer gets the gist that Frank is going for the third.
Dial-Up Access - Season 4, Episode 13
Frank is a nostalgic guy. In fact, the show frequently points out how he is stuck in a state of arrested development. An example of this is his relationship with a former teacher, Lynn Onkman. While it's doubtful this plotline would be a part of any modern sitcom's narrative (in spite of the fact that 30 Rock is fairly recent), it does shed further light on why Frank wears the hats.
"Dial-up Access" is indicative of Frank Rossitano reaching out to society. His hats are his form of communication. Like all clothes, they're an extension of a personality; Frank wears his personality on his sleeve — or head. His "Dial-up Access" hat is the best of 30 Rock's fourth season.
Horny - Season 3, Episode 1
Liz Lemon has had her spiteful moments, but Frank's move with the "Horny" hat is the king of spite. Liz is trying to adopt a child, and in order to do so, an adoption agent must visit the set of TGS in order to determine both the level of safety in the workplace as well as Liz's demeanor at work.
While trying to straighten up the TGS set, Liz barks at Frank to take off his hat, which reads: "Horny." It would be a poor look not only for her but for the cast and crew as a whole. Frank, in hilarious form, changes to a hat of a different color, but the slogan remains the same.
Bigfoot Expert - Season 1, Episode 4 & Season 1, Episode 7
It's fun when one of Frank's hats makes a return appearance. The bright yellow "Bigfoot Expert" hat made two appearances during the premiere season. The hat is memorable mostly due to its prescience.
One of Frank's best episodes (if not his best, overall) was season 3's thirteenth episode, "Goodbye, My Friend." Jack tries to get Frank back into law to achieve his true purpose in life. The narrative equates this mentorship to the plot of the bigfoot movie Harry and the Hendersons in a way every 30 Rock fan can appreciate.
Trap Do r - Season 2, Episode 13
The best Frank hats are also his most creative. "Trap Do r" gives the viewer the impression that Mr. Rossitano makes them at home. It is as if he stitches together each one and devotes ample creative energy to come up with their unique slogans.
Each one of Frank's hats serves as a brief illumination of his psyche. "Trap Do r" shows that he is a creative personality, tying in nicely to the fact that he writes for a sketch comedy show.