It’s hard to imagine a world without Patton Oswalt’s comedy, and there’s no way to deny his ongoing legacy. Through his unique blend of observational and confessional humor, Oswalt has become a household name over the past few decades, and it’s truly been a treat to watch him evolve as an artist and storyteller. Over the years, we’ve seen a single and unattached pop-culture nerd blossom into a husband, father, and storytelling extraordinaire.
With each special, we learn more about his life (as he tells it), and get a profound insight into how his mind works. Though he has gotten a little more tame and calculating with age, his comedy is as sharp, poignant, and self-aware as ever. It also goes without question that with each hour-long special that he puts out, that he still has plenty of stories to tell, and we’ll continue to chomp at the bit as long as he’s actively working as a stand-up comedian.
With that said, we’re going to rank 10 of Patton Oswalt’s best comedy specials.
10 Patton Oswalt: We All Scream (2022)
We All Scream is Patton Oswalt’s most recent hour-long special, and it just goes to show you that some comedians continue to get better with age. Okay, well the jokes get better, but life sometimes gets worse. Just like 2020’s I Love Everything tells us about the woes of being a man in his 50s, We All Scream gives us some very relatable examples that only benefit from Oswalt’s delivery.
But in many ways, this special also falls flat. Though Oswalt has been revered for leaning into absurdist and surreal imagery, he also drags out some of his bits in a way that he hasn’t in the past. The opening monologue about a barn full of clown pubes could have been more impactful if it was cut shorter, but instead of segueing into a different bit, he ends up beating a dead horse. He does bring it back, but not with the pacing that we’ve been familiar with up to this point in his career.
We All Scream isn’t necessarily Oswalt’s finest hour, but it’s familiar, it’s funny, and it continues the story that he’s been telling all these years. In other words, it’s a worthy addition to his cannon, and gives us reason to believe that he’ll continue to wow us with more specials for years to come.
9 HBO Comedy Half-Hour (1997)
The Patton Oswalt that we were introduced to in 1997 has all the elements of a great comedy special, but it’s clear that he was still cutting his teeth and honing his craft. The growing pains of an up-and-coming comedian are all present, but still, he kills it. You’ll notice that later in Oswalt’s career, his comedy skews more toward a confessional type of style, and he tells heightened versions of stories based on his own life as a vessel to deliver joke after joke. This HBO special, on the other hand, is more rooted in observational humor, but Oswalt’s unique voice and delivery is enough to make us want more.
Though Oswalt’s Comedy Half-Hour suffers from a number of familiar observational stand-up comedy beats (i.e. New York versus LA jokes), his deep knowledge of pop culture, and his ability to extrapolate everyday situations to the point of absurdity shows us the mind of a serious comedian at work, and the special still holds up to this day.
8 Comedy Central Presents (1999)
Oswalt’s Comedy Central Presents special made its rounds when he was 30 years old, and we see a tighter, more focused set with excellent pacing. Though we’re still very much in the observational comedy territory, we see a stronger narrative structure than what’s found in his HBO Comedy Half-Hour special. We also get dialed into some more political humor, but it never comes off as too heavy-handed.
And just like the HBO special, we see Patton Oswalt do what he does best, and extrapolate to absurdity. One notable instance of this method of joke delivery is illustrated through Oswalt’s frustration with the Easter egg-dying company, Paas. Through this legendary bit, we learn that several other companies popped up in the '70s, and attempted to “unseat the Paas dynasty.” Oswalt asserts that after several companies tried to innovate in the egg-dying industry, Pass still remains untouched.
7 Patton Oswalt: No Reason to Complain (2006)
No Reason to Complain is a special that suffers from joke exhaustion, but this isn’t necessarily the fault of Patton Oswalt. Let’s break it down real quick:
In 2003, Oswalt recorded a 222-minute album, aptly titled 222. This album is an absolutely unhinged and unedited set that includes what seems like every single joke Oswalt had worked on for the past few years. What’s more, Oswalt gets progressively more drunk on wine throughout his performance. 222 was edited down into a more cohesive album called Feeling Kinda Patton, which comes across as a tighter performance, but loses the manic charm that the unedited album is celebrated for.
That brings us to No Reason to Complain, which in many ways is an edited-down version of Feeling Kinda Patton. Make no mistake, No Reason to Complain is a solid special, but a few years have passed, and you can tell that he wanted to work on more new material at this point in time. Though we hear some familiar bits from the original 222 album, we do get new material in the form of Oswalt suggesting that reality TV will come to an end once producers have filmed every single aspect of reality, and we start to see more Lord of the Rings references creep into his set.
As for the older material found on this special, it’s executed flawlessly, and to a very receptive crowd. But in the case of his hair-metal bit that riffs on the dubious sexuality of bands like “Jackyl, with a Y,” you might want to go back to the original 222 set to hear an inebriated Oswalt deliver the material with just a little more venom.
6 Patton Oswalt: Talking for Clapping (2016)
Talking for Clapping is in many ways a celebration of Oswalt’s reluctant transition into middle-age territory, but is also deceptively optimistic in its delivery. Though Oswalt finds himself crippled by his anxieties, he’s still confident in his storytelling, and he leaves us bits that have very satisfying payoffs.
Though Talking for Clapping has its ups and downs, his story about attending a child’s birthday party when a clearly hungover clown shows up late to make balloon animals is enough to make you want to stay engaged. Throw in a legendary story about one of his worst gigs (in which he craps his pants on stage), and a very self-aware acknowledgment of his politically driven discourse on Twitter, and you’ve got a solid special.
This may not be Oswalt’s best special, but think of it as a later in career album from a band that you love to listen to. It might have a lull at some point throughout its run, but there are plenty of worthwhile bangers that make you want to keep it in rotation.
5 Patton Oswalt: I Love Everything (2020)
I Love Everything brings us to a better place than where 2017’s Annihilation left us, and it’s clear that Patton Oswalt has broken through the grief of his wife’s passing, and still knows how to deliver the goods. Oswalt has stated in interviews that his grief forced him to evolve, and we witness a man who has done just that. At the age of 50, Oswalt finds a healthy mix between the observational comedy found earlier in his career, and the confessional humor that we’ve become familiar with over the decade that preceded I Love Everything.
One second, we’re getting a recounting of Oswalt’s experience attending his daughter’s second-grade art show, and before we know it, we’re being bombarded with the strange underworld of independent subcontractors hanging up wallpaper in his new house. But what seals the deal is Oswalt’s story about taking his daughter to Denny’s, and the existential crisis that follows.
4 Patton Oswalt: Tragedy Plus Comedy Equals Time (2014)
Though it took a few years for Patton Oswalt to follow Finest Hour with another hour-long special, he does not fail to deliver on this one. We’re met with an older, and wiser Patton Oswalt, and much of his humor is still deeply rooted in his family life. It’s evident that he’s doing the dad thing the best he can, but still has a number of insecurities that he admits he still needs to address.
Much like we hear in My Weakness is Strong, we are clued into another recurring fantasy that Oswalt had about his depression. In an expertly paced seven-minute bit, he describes how he once thought about killing himself at the grocery store while shopping for Lean Cuisines and listening to Toto’s “Africa” while standing in a daze in the freezer aisle.
Though this is one of his darker bits, there is a level of humanity that makes the story land. The fact that Oswalt is able to make light of his mental health issues in such an off-the-wall way not only makes the story extremely relatable, but tells us that we’re not alone in our struggles. In other words, his difficulties with depression, a through line that he often revisits throughout his specials, always resolve in a way that tells us that everything is going to be okay. And if we’re not okay, we can still relate to his low moments because he makes it clear that there is a light at the end of the tunnel.
3 Patton Oswalt: My Weakness Is Strong (2009)
2009’s My Weakness Is Strong is a powerhouse hour-long special that comes with strong recommendation, and for a few different reasons. First off, this is the last special that Oswalt put out before becoming a father, which happened shortly after My Weakness Is Strong was taped. And the anxiety Oswalt has about his quickly approaching paternal responsibilities carries the show.
We learn about Oswalt’s ongoing struggle with depression, and he paints quite the picture in his explanation as to why he needs to work through some of his personal issues before his daughter is born, because he doesn’t want his daughter to witness some of the lows that he experiences during a depressive episode. Oswalt asserts that he wants to stop taking Prozac, because he knows that when we finally end up living in a dystopian hellscape like the one portrayed in the Mad Max movies, that he needs to be in shape, optimistic, and not used a sexual incentive for the marauders to scavenge for fuel for their nitro trucks.
It’s this dark, post-apocalyptic fantasy that tells Oswalt that he needs to improve his outlook, and lose some weight, so he could be the parent that he thinks he needs to be. My Weakness Is Strong is the moment that Patton Oswalt became a little less observational, and a lot more personal, and for that reason, it’s one of his stronger specials.
2 Patton Oswalt: Finest Hour (2011)
Finest Hour picks up right where My Weakness is Strong left off in the sense that Patton Oswalt now has the experience of being a new father under his belt. And though he was able to squash some of the anxieties that he had voiced previously, a whole new level of concern is iterated. The special opens up with a story about buying a bunch of magazines for his wife, while wearing a matching gray sweat-suit, while in a fever-pitch of exhaustion that’s all too familiar for new parents. He even goes so far as to suggest that his outfit looked like a rough-sketch made by "Dr. Seuss on an angry pussy hunt.”
But Finest Hour isn’t just about the trials and tribulations of being a new parent. At this point in his career, Patton Oswalt has nailed down his narrative formula, and his storytelling only continues to improve from this point forward. One of the more notable incidents from his life that he recalls involves going to see Jerry Maguirewith his brother on Christmas in LA, and the imagery he conjures up while describing his enjoyment of the movie, and his brother's seething hatred for it brings the house down.
It’s safe to say that Finest Hour is truly one of Patton Oswalt’s finest hours, and this is one of those comedy specials that you can watch over and over again without it ever getting old.
1 Patton Oswalt: Annihilation (2017)
This may very well be the hardest Patton Oswalt special to listen to, but not because it falls short of expectations in any way. Annihilation is the first special that Oswalt taped after his wife, Michelle McNamara, suddenly passed away in 2016. The first half of the special takes us to familiar territory, and we hear the jokes about parenting, political strife, and pop-culture that we’ve come to expect from a Patton Oswalt special.
But when we get past the halfway point, Oswalt lets his guard down and walks us through his personal tragedy in a way that’s gut-wrenching, painfully self-aware, but also hilarious in its own right.
Annihilation is as thoughtful and heartfelt as it is cathartic, and you just have to witness this emotional rollercoaster to truly feel its impact. He closes this special with his wife’s motto about life: “It’s Chaos. Be Kind.” This isn’t the kind of comedy special that you throw on during your morning commute to get some laughs in before work, but it’s Oswalt’s best special, and comes with strong recommendation if you’re in need of a relatable way to cope with your own personal tragedies.
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