Ranking Patton Oswalt's Comedy Specials and Albums

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Over the last few decades, Patton Oswalt has steadily become one of the best stand-up comedians of his generation—and one of the most successful ones, at that. With a lineup of incredible specials, film and TV roles and bestseller books, Oswalt has found success in a myriad of mediums and shows no sign of stopping down. With his latest stand-up hour-long Talking For Clapping premiering on Netflix last month, let’s take a look at the stand-up career of Oswalt by ranking all of his specials.

11. HBO Comedy Half-Hour—1997

Patton Oswalt’s first special, an HBO Comedy Half-Hour from twenty years ago, shows Oswalt as a young comedian still finding his voice. Already you can see elements of where his stand-up will go at points, from his announcement at the very top that he doesn’t have any segues, to his occasional outbursts, but this is Oswalt still discovering what works for him. This also is his material that has aged the poorest, with Oswalt proclaiming he looks like a little lesbian, engaging in his early material’s obsession with midgets and references to Hanson and Xena, Warrior Princess. Even the material that he uses in later specials will be stronger in those sets, like his jokes about Carvel ice cream cakes and “Piss Drinkers” magazine. In hindsight, it’s fascinating to see how Oswalt has grown as a comedian from here, but maybe the most interesting aspect of his first special is the way it opens, with Oswalt and other then-young comedians who had HBO half-hour specials that season, like Jeff Garlin, Harlan Williams and Dave Chappelle, sitting around discussing comedy.

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10. Comedy Central Presents—1999

In his Comedy Central Presents half-hour special, we start to see a more recognizable version of the stand-up we know and love today, with the personality and interests that still define him coming into clearer view. Oswalt talks about his love of cinema for the first time, but more importantly, this half-hour shows Oswald’s ability to build a joke and increase the idea into something great. His take on war reporting might be the first example of this, but also his frustration with egg dying and a trip to Amsterdam allows Oswalt to take a simple premise and expand upon it in a way that no other comedian can.

9. Patton Oswalt: No Reason to Complain—2006

Oswalt has stated in interviews how he was unhappy with how No Reason to Complain came out, since it only allowed him to have a half hour of new material, combined with a half hour of material he first released four years prior. No Reason to Complain is very much a pared down, tamer version of his Feelin’ Kinda Patton album, which was already cut down from 222. But that new half hour features some excellent new bits, such as his problems with reality TV, the sustainability of NPR and his admiration for Mel Gibson and the balls it took to make The Passion of the Christ. Oswalt has said that this was the last time he made a special on someone else’s schedule and you can hear a slight exhaustion in the older jokes, but combined with the newer material, No Reason to Complain plays like a greatest hits of his last few years, mixed with some great new stuff.

8. Feelin’ Kinda Patton—2004

Much like how No Reason to Complain is a pared down version of Feelin’ Kinda Patton, Feelin’ Kinda Patton is a shorter version of the much longer 222. Because of that, Feelin’ Kinda Patton is much better edited and better paced than 222, yet it misses the scope of that album’s greatness. Performing in Athens, Georgia’s 40 Watt Club, it’s as if Oswalt finally finds the sweet spot of his comedy, where he can be angrier, more political, frustrated and referential in ways that he didn’t dare to prior. If you’re looking for an introduction to the comedy of Oswalt, there might not be a better place to start than Feelin’ Kinda Patton.

7. An Evening with Patton Oswalt—2007

As a pack-in DVD that came with Werewolves and Lollipops, An Evening With Patton Oswalt takes him back to the 40 Watt Club to prepare the material that would eventually go on that album. An Evening with Patton Oswalt is definitely rough around the edges compared to the album that would come from that same material, but that’s exactly why it exists: a way to shine a light on the process that leads to a recorded special. Adding to that rough around the edges feeling is the fact that during the show, a man pisses on another person and the carpet catches on fire. It’s not the best of Oswalt’s live, unedited specials, but it’s surely the most eventful.

6. Patton Oswalt: Tragedy Plus Comedy Equals Time—2014

In Tragedy Plus Comedy Equals Time, we see a man completely different than the man we met almost twenty years ago with his HBO special. Directed by Bobcat Goldthwait—the only time Oswalt has had another comedian direct one of his specials—we see Oswalt discussing much tamer subjects than we could’ve ever imagined him covering in the early days, such as becoming a decent father and the lack of hatred towards music that you don’t appreciate. But while it may seem like the polar opposite of what originally drew audiences to Oswalt, it’s also one of his most candid, open specials, as he continues his discussion of his depression, losing weight and getting a hooker in Germany. Tragedy Plus Comedy Equals Time also has Oswalt telling a fantastic story about performing in Las Vegas to drunks that could not have been told when he was younger; he wouldn’t have been able to build it as brilliantly as he does without decades of experience under his belt.

5. Patton Oswalt: Finest Hour—2011

For the first time in Patton Oswalt’s specials, Finest Hour is less about him and more about the activities of his newborn daughter and how that experience has changed him. Of course this appears in stories that involve his daughter, such as how he’s constantly hallucinating from lack of sleep, wearing sweatpants and defending his parenting style against his parents. But it also feels like because of this newfound responsibility, Oswalt is maturing—not in a bad way—as his stories and jokes become slightly softer but still as biting, especially when talking about gay marriage and religion. If anything, this evolution of Oswalt shows him as a comedian that has honed his craft with impeccable writing and a distinct viewpoint that can withstand age, life changes and huge evolutions in who he is.

4. Talking For Clapping—2016

Oswalt is still working at the top of his game these days and is taking some chances he might not have in the past. It’s that confidence that Oswalt has that is the biggest takeaway from this special. He knows how good he is at his job. Good enough to thread bits of sociopolitical commentary in among other material about his failings as the man of the house and a pitch perfect closer that tells of the worst birthday clown of all time. He’s also smart enough to point the gun at himself throughout, telling us of his worst stand-up show and going off book to mock his propensity for perspiration.—Robert Ham

3. 222—2002

222 is a sloppy, two-hour-plus manic fit of a comedy special. But chronologically, it’s also the first time you can hear the brilliance of what will come from Oswalt’s comedy, and the unedited mess gives the full experience of seeing Oswalt live at that time in his life, frustrated and drunk on wine. 222 would be edited down to become Feelin’ Kinda Patton, but that tightly-edited album loses some of the magic. 222’s beauty is in how freeform it is, with Oswalt coming into his own and finding his voice for the first time, the angrier, more political, comic book and film nerd that we will hear him become. Even though there is a fury as Oswalt compares George W. Bush to Darth Vader and hoping that the apocalypse will come soon, there’s also an inherent warmth for the audience and his opportunity to tell jokes for a living. In between mocking his equally drunk photographer and doing requests for the audience, you can see the dichotomy of Oswalt: the man who’s exasperated with the world, but excited about the opportunity that world has given him to do what he loves.

2. Patton Oswalt: My Weakness Is Strong—2009

After complaining about relationship problems and Bush in the past, My Weakness Is Strong finds Oswalt married and excited about the new president, but also with a new amount of success. My Weakness Is Strong is Oswalt post-Ratatouille, dealing not only with the children that love his character but also rats in his backyard, in one of the special’s funniest bits. This is also Oswalt right before his life is about to change, as he announces that his wife is pregnant with their first child—a huge change that will become a large part of his upcoming specials. Oswalt has gone into aspects of his life before, but never before as much as he does here, where he contrasts his depression with the surprising amount of hope for the future found throughout the rest of My Weakness Is Strong’s material.

1. Patton Oswalt: Werewolves and Lollipops—2007

In 222, Oswalt stated that love and happiness is the death of comedy, yet proving himself wrong, Werewolves and Lollipops—the first album after getting married—is also Oswalt’s masterpiece. Every single track on Werewolves and Lollipops is excellent, with Oswalt at the height of his game. Here Oswalt doesn’t rely on pop culture references as much as he usually does, but still embraces his loves in his comedy, like when he discusses how he wants to kill George Lucas with a shovel. But Werewolves and Lollipops works because it feels more personal and less observational than his other albums. Werewolves and Lollipops has Oswalt discussing his new marriage, his struggle with weight loss and the anger he feels towards his hometown, and he even finds time to destroy an impatient heckler. With Werewolves and Lollipops, Oswalt finds the ideal blend of anger, cultural frustration, personal stories and insanity that make Oswalt one of the greatest stand-up comedians today.

Ross Bonaime is a D.C.-based freelance writer and regular contributor to Paste. You can follow him on Twitter and you can find more of his writing at RossBonaime.com.

Ranking Patton Oswalt’s Comedy Specials and Albums