Tommy Little: Pretty Fly for A Dickhead Review – A Stand-Up Comedy Special That Lacks a Purpose

By Marc Miller
Published: May 5, 2023 (Last updated: May 11, 2024)
Tommy Little: Pretty Fly for A Dickhead Review
Tommy Little: Pretty Fly for A Dickhead Promotional Image (Credit to Prime Video)


Tommy Little has an infectious personality and excels when engaging his audience, but his Prime Video standup comedy special lacks genuine purpose.

The best stand-up comedy specials often stem from a place of pain, featuring authentic pathos that resonates with viewers in the audience and at home. However, Tommy Little: Pretty Fly for a Dickhead, while a bit chaotic, features a likable performer who keeps his audience at head-scratching arm’s length.

The 35-year-old Australian comedian Tommy Little probably gained his greatest fame for co-hosting his popular radio show, Carrie & Tommy. The title of his special is not exactly articulate or even modern, but it reflects an act that’s a bit of controlled chaos that’s self-contained to a point because the material has nowhere to go because of the lack of maturation.

I have been watching some great comedy specials lately. Selective Outrage or John Mulaney’s brilliantly constructed Baby J are hard to compete with. Those acts came with buzz-worthy social media and newsworthy tabloid fodder. Yet, those acts have the depth that Little’s act lacks.

However, a comic takes the listener on a ride where they wonder about the destination until the point of their hilarious and deeply felt journey becomes clear. Here, Little’s bits come across as stories you would repeat with old friends you’ve heard numerous times before. Little rarely enters territory that feels relevant or authentic to his life.

And when he does, for example, in a touching scene with his father, the moment is frustratingly inert. That’s not to say Little doesn’t have his charms. Little is an energetic and engaging performer who excels at connecting with his audience with his carefree attitude.

While his shtick can come across as fratboy-ish, he has an endearing rapport with his fans. He often delivers his best jokes through off-the-cuff moments like dealing with lifelong asthma or simply playing with the audience’s reaction.

Tommy Little is a likable comedian. However, his stand-up special Pretty Fly for a Dickhead is relatively average. This is disappointing for a comedian with a contagious personality and a handful of jokes showcasing his self-deprecating style. Unfortunately, his personal stories have worn out their welcome and need fresher material.

Pretty Fly for a Dickhead is worth watching strictly if you are a fan of the performer or a diehard fan of the anecdotal comedy genre. Tommy Little’s latest stand-up comedy special lacks genuine purpose.

That being said, the stories Little tells are prolonged and overdone. For instance, the nearly 20-minute jet ride story or how he smuggles drugs across customs. Those are too loose, meandering, and need to be tightened up for a more significant payoff.

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