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30 Rock: Frank's Most Iconic Hats, Ranked

Frank Rossitano (played by Judah Friedlander) was one of the lead writers on the fictional SNL-esque TV show from 30 Rock and a series mainstay, appearing in every episode. He’s an almost-admirable schlub and self-confessed dirtbag but his defining attribute would probably be his customized hats. In one of the many style choices that Friedlander incorporated into his appearances as an actor and stand-up comedian, Frank is rarely ever seen without one of his iconic hats on.

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Coming in many shapes and sizes, and a seemingly infinite number of colors and slogans, the hats became kind of like Bart’s infamous chalkboard from the opening of The Simpsons – with a new gag appearing on at least one at some point throughout each episode. Here’s our collection of Frank’s most iconic hats from 30 Rock.

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10 Horny

Need we say more? Probably, yes. The Horny hat leaves little room for interpretation, admittedly, but it is a great place to start in describing the garment choices of Frank Rossitano. Firstly, it shows Frank’s dedication to communicating useful information through his hats. No one will be able to say that they were unaware of Frank’s horniness and there’s a certain degree of social utility in that.

Secondly, it shows Frank’s flexibility with his hat choices and his willingness to change. After being told to change his hat by his boss, Liz Lemon, Frank does, indeed, change his hat to the next entry on our list.

9 Horny 2.0

The second iteration of the Horny hat – because one could never be enough – screams that Frank Rossitano’s desire for loving is matched only by his desire for humorous hats. In a more refined Derby configuration, compared to the subsequently-outmoded original, the Horny hat 2.0 illustrates Frank’s unshakable determination in conveying his unceasing horniness.

The sleeker styling also makes the hat an ideal fashion choice for an important romantic date as it demonstrates a certain level of worldly sophistication. One which is only marred slightly by the fact that it has the word HORNY written on it in giant letters.

8 Harvard

The Harvard pork pie hat comes about as a form of mockery towards his co-worker, T0ofer, and his propensity to drop the name of his alma mater whenever he can shoehorn it into the conversation. Toofer responds by dressing as Frank with a hat emblazoned with “Mom Expert”. It’s a little on-the-nose, and not quite representative of the overall care and artistry that goes into Frank’s hats, but it’s a solid piece, regardless.

The Harvard hat is not complete without the accompanying scratchy-looking suit-tie-vest combo, thus making it one of Frank’s more complex overall outfits and possibly the most amount of clothes he’s ever shown to wear in the show at one time.

7 Brain Masala

Some of Frank’s hats are more enigmatic than others. Some are riddles or plays on words and grammar to comedic effect. Some of them are just kinda gross and self-explanatory. A brain masala, however, does sum up the unfathomable, and mostly undesirable, mind nesting beneath the hat.

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It could, on the other hand, be an expression of Frank’s unusual culinary tastes. Drawing attention to society’s assumptions about the overall palate, and adventurousness, of a proud working-class Italian-American man like Frank Rossitano. But, yeah, he’s probably just being gross. Especially because he knows other people have to look at it while they eat in the office.

6 Panic Dream

Reality is just too small a box to attempt to place Frank’s hats into. Complete with aghast skeleton, the Panic Dream relays our human fears in an elegantly simple piece of headwear. Whether you’re going through a stressful time, or just a generally anxious person, Frank’s Panic Dream hat is hugely relatable.

The Panic Dream hat doesn’t actually appear until one of the final few episodes of the series, but we’re very glad it did. Even though it’s not technically a hat that Frank wears in the reality of the show, but in someone else’s own panic dream, we’re still fairly certain that it counts.

5 Shark Cop

This one really raises more questions than it answers. Is it about a cop who polices sharks? Is it about a shark who is a cop? If so, does the shark police people or other sharks? Are there shark laws? Did they go to shark police academy or was this position self-appointed?

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It could be a pitch for a movie or TV show about any of those things. It could be a demand. It could just be gibberish. But the point is – we don’t know and it’s exactly the kind of tantalizing premise that can drive the imagination mad.

4 Sitting Ovation

A true tour de force of Frank’s witty hat-wearing versatility. The Sitting Ovation piece is one of the most worthy contenders to be stored in the vaults of the American National Archives for future generations to both enjoy and learn from. It’s a near-perfect representation of the reserved attitude that was so prevalent in culture and fashion at the beginning of the decade. That and it’s pretty funny.

The hat holds a special place also, as it appears in the bumper double-bill to celebrate 100 episodes of the show. A milestone not just because of the actual achievement in production but also because 100 episodes is generally considered to be the point at which syndication becomes guaranteed. That’s certainly worthy of some kind of ovation.

3 Letters

The Letters hat is open to many interpretations. Is it a commentary on metanarratives within today’s society? Is it a musing on the inconsequential nature of the written word within fashion itself? Perhaps it’s a meditation on the lack of the thought-out, long-form, eloquence that was once prevalent in the handwritten letter but has now been lost in the digital age of texting. We daren’t limit it to just one thing.

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What we can say is that it cements Frank Rossitano as an unknowable intellect. Not a man to be fully understood – certainly not within his own time – but one to be appreciated nonetheless.

2 And

Short. Bold. Simple. To the point. The And hat requires no real explanation. You could call it a wearable conversation piece. You could call it an emphatic statement to silence all of those around you. A hat that says “I make no excuses for who I am.” A hat that says “This is me and what of it?”

The conjunctive is the English language’s greatest unifier. It’s a tool used to search for more out of conversation, out of life and out of the universe. Now, thanks to the brilliant mind of Frank Rossitano, it is also a hat. Truly inspiring.

1 Why.

Why. That is the question. But, as you can see, in this case it is not a question. Simply a statement. Perhaps Frank’s most profoundly philosophical piece of attire, the Why. hat understands that to ask “Why?” of creation is a futile act, yet the yearning for knowledge remains.

In many ways, it perfectly sums up Frank Rossitano. It shows him as a man on a spiritual pilgrimage, open to answers from anyone who meets him and has the privilege to look upon his hats. It has certainly been our privilege to do so and we hope that he found the answers that he sought.

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