Patton Oswalt Albums Ranked
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Patton Oswalt is my favorite comedian. He’s been a favorite ever since I see him do the Black Angus Steak bit at Irving Plaza, like, fifteen years ago? But he’s been in pretty heavy rotation for me on Spotify during work hours (the life of a front end developer allows for such indulgences).

In addition to having zero prestige, being my favorite comedian is also a poisoned chalice as it has been occupied previously by Bill Cosby, Woody Allen, and Louis CK. I’m not arrogant enough to think that my admiration could actually precipitate another person’s sex crimes and there have been other favorite comedians in the past who seem to be assault free (Chris Rock and Maria Bamford, you’re both cool… so far but I’ve got my eye on you). I just hope Patton stays clean.

I’ve always loved his geekiness and his wordplay and if ever there were a comedian that I wanted to be, it would probably be him. So, because I’m a left brained geek, I’m going to rank the thing I love. Here we go.

(I’m leaving Annihilation – the special dealing with his first wife’s untimely death – out of the running right now. I haven’t watched it enough to get it into my system like the other specials. Much like Hannah Gadsby’s Nanette, it seems like some comedy specials deserve a different kind of consideration.)

Frankensteins and Gumdrops (EP)

https://www.youtube.com/watch?v=0h0J1sphPu4

I don’t own this album, I just happen to have found it on youtube. It may not even have ever been a physical EP and the second half of it is about the MegaLeg, which he discusses at the end of Finest Hour but the Daniel Plainview (Daniel Day Lewis in There Will Be Blood) impression in the first half kills me every time. If you haven’t heard that bit, do it now. Seriously, right now.

Werewolves and Lollipops

I assume that Frankenstein and Gumdrops was done around the same time as this album given the similarity of the names. This is Patton’s sophomore effort after Feelin’ Kinda Patton. It’s solid but it’s always had that second album feel to me. As the saying goes, you have your whole life to make the first one and then six months to make the second one. “You Are Allowed 20 Birthday Parties” always struck me as a half baked bit. But there are some strong ones on here: “Physics for Poets,” “Clean Filth,” and “Death Bed” hold up pretty well.

My Weakness is Strong

This is Patton’s third album and honestly it feels a little interchangeable with Werewolves and Lollipops. It’s kind of like Patton’s Kid A and Amnesiac. Yeah, they’re two separate albums but they were the same phase and recorded around the same time. His “Sky Cake” bit is a little disappointing in its lack of anything new to say about religion. His Obama material seems a little dated now. “The Oswalt Family Crest” has always been a little too similar to a Dana Gould bit for my liking. “Rats,” “Orgy,” and “Space Robot” are perennial favorites but the coup de grace of this album, the bit that puts it ahead of Werewolves and Lollipops is “The Magician.”

Incidentally, this album also starts streak of including a bit about needing to lose weight.

Talking For Clapping

This special was recorded in San Francisco and is still available on Netflix. I think I’ve listened to it a hundred times. This album finds him still happy with domestic life which is heartbreaking in retrospect because it’s the last special he recorded before his wife died. Apologies for the sad note but make no mistake this album is great. Personal highlights from this album: “The Worst Show I’ve Ever Done,” “My Little Pony,” and “The Silver Balloon.”

Tragedy Plus Comedy Equals Time

This album edges out Talking for Clapping only because of “The Sellout,” the strongest track on the album. “My Prostitute” and “New Clothes” are favorites too.

Feelin’ Kind of Patton

This is the album that started it all for me. It’s his first. I bought it on CD. I wore it out. It has “Steak” on it, i.e., The Black Angus Steak bit. “My Christmas Memory” can still make me laugh randomly if it pops in my head. There’s too much here that’s great to mention. It does suffer from the use of the r-word and the word midget, showing it’s 2004-ness. If you listened before those were taboo, you can perhaps forgive it. If not, it may be harder to enjoy. This is still a great album, though.

Finest Hour

This album is dead center of Patton’s oeuvre. There’s something about that period for an artist. It’s where they’re at the height of their powers and have yet to get so bored with themselves that they start getting experimental. I recently revisited this album and realized that I love every track on it. And it ends with the one two punch of “The Best Comedy I’ve Ever Seen” and “The Horror of New York City.”

222 (Live & Uncut)

I have to be honest, this is a douchey pick for best album because it’s really just Feelin’ Kinda Patton unedited. It’s all the same bits but you get to hear them with the banter and the mistakes and out of order. It’s Patton’s Slanted and Enchanted. It’s raw and a little sloppy at times but that’s what makes it great. You feel like you’re there at the roughly two hour show.

Thank you for reading through this list that no one was asking for. As a bonus, please enjoy the extended bit below. It’s another favorite.

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