I’ve written a couple of posts now about sketches. Key and Peele sketches and some random SNL sketches but I wanted to write a definitive all time favorite sketches post.

I started the list and let it breathe for a bit. I mean this is my all time favorite sketches, I have to make sure I’m considering all of them.

As I assembled the list, though, I was realizing that it was more like a list of the most important sketches. The sketches that were coming to mind were the ones that made me laugh the hardest the earliest and made me love sketch comedy or they were ones that made a huge impact when they came out. Still others are so popular that their inclusion here will seem almost trite. And there are a few that I simply love (yes, person who knows me well, those are The State sketches).

The criteria wasn’t just “Is this one of my favorites?”, it became, “Were my friends and I quoting it in the halls in between classes in high school? Did it change the way a lot of future sketches were done? Was it just really really good?”

To the dismay of any sketch comedy fan, there isn’t any Monty Python, Kids in the Hall, or In Living Color but so it goes. Now, here they are, in no particular order, my favorite slash most important sketches.

Adam Sandler – “They’re All going to Laugh At You”

Okay, so, this album does not hold up. If you haven’t heard it, you don’t need to. But if you, like me, were a teenager when this album came out, I’d be willing to be that you laughed pretty damn hard at it. So, including this is like including 2 Live Crew on a list of your most important hip hop records. Yeah we listened but we also learned better. But the line in the song above, “See that shapoo bottle? Now stick it up my ass,” made me laugh as hard as I’d laughed to that point in my fifteen or sixteen years. I originally picked “Toll Booth Willie” as the sketch but really it’s all of them, the Severe Beatings, the Buffoon. This album is dumb and it’s hilarious.

Taco Mail

One of the reasons I’m so obsessed with The State is that even in a world where every piece of content seems to be available online for free, you still can’t find the original State sketches. They all contained so much music that the cost of the rights has prevented them from being released in their original form. There was also a time when you couldn’t count on seeing anything and everything you ever loved online again. It was during this time (the early aughts) that I bought Skits and Stickers, a VHS tape that was the best of The State. It included the above sketch, “Taco Mail.” I didn’t get it at first. It takes a while to realize that there’s nothing to get, it’s just a dumb premise. A mailman delivers tacos instead of the mail. But the gravity that they give it is so amazing. And Kevin Allison’s, “You’re not gonna eat that crap are ya?” I can’t embed it but you can view it here.

Wayne’s World

Mike Myers’s sketches were always brilliant. I loved Sprockets too. They were distinct, in a clear voice, and endlessly quotable. (They were also endlessly repeatable too, which is a bit of a drawback to his style but nothing’s perfect.) Party on, spew, hurl, we’re not worthy, schwing, sphincter – all of those were in the vocabulary of my friends and me. The above sketch is probably the best representation of Wayne’s World, with both Tom Hanks and Aerosmith and the pretty brilliant Communist question curveball (similarly repeated by Alice Cooper’s Milwaukee monologue in the movie). Wayne’s World meant a lot to me as a kid.

Lazy Sunday

The Lonely Island (along with Donald Glover’s sketch group Derek and Bo Burnham to name a few others) got in on youtube when the getting was good. They also wrote song parodies that sounded like real songs and it landed them on SNL (Andy was the only cast member but Jorma and Akiva were writers). I watched “Lazy Sunday” countless times. So did everyone else. We take viral sketch comedy for granted. I worked at Comedy Central briefly and a big topic of discussion was how to stop our content from being taken by YouTube. That was a long time ago and those days are over. Everyone cooperates now and this video was one of the first to do so. The sketch was clearly filmed by friends in the hopes that it might make it past Lorne Michaels but I think it still holds up.

Matt Foley

I’m pretty sure that I saw this live and remember thinking that it was one of the funniest sketches I had ever seen. This definitely falls in obvious category but it’s become ubiquitous because it’s so good. (Also, Christina Applegate deserves more credit for comedy. She was also in Anchorman for Christ’s sake.)

Telephone – Nichols and May

These people, among others, started improv. Mike Nichols then disavowed improv for scripted content but the sketches he made with Elaine May are still great. My mom got me this album for Christmas one year. When the angelic Miss Jones comes in, “Yes yes I’m here!” it’s perfect. This sketch also contains – to my knowledge – the first use of the bit, “That is ‘k’ as in ‘knife’…”

More Cowbell

This is prime Will Ferrell who is one of the greatest SNL performers of all time. It’s also in the obvious category. It may have been quoted endlessly on morning talk radio and featured on tacky t-shirts on frat bros but let’s try to think back to the first time you saw it. I remember thinking, “Oh yeah, there is a vague cowbell in the background of that song.” And the first time Christopher Walken said, “It was sounding great but I could have used a little more cowbell,” you laughed. Yes you did because it was just too damn good.

Bookworm (aka Barry Toink)

This was another State sketch filled with pop songs and is thus impossible to find anywhere. It’s on the DVD but it’s not the same. The above picture was the only evidence I could find of it online. You are a genius, Joe LoTruglio. It featured dumb jock Barry Toink’s epic quest to name the guy who can’t KEEP HIS FACE OUT OF BOOKS! Temper check… okay. (Yeah, those are lines from the sketch.) And the one line of dialogue that I will love until my dying day, “Silver medal try but no, adios-ay lad-ays, I must go seek knowledge and it’s bastard son, Truth.”

The Audition

I didn’t care for Mr. Show that much when it was on HBO. I think it was a little jarring to have sketches not end and just transition into the next sketch. It wasn’t until I started taking sketch classes and writing sketches that I realized just how good the show was. “The Audition” might be the perfect sketch, for its pacing, it’s build, and its payoff. It always gets me.

Doug

As I’ve said about The State, part of the appeal of the show was that it was ours. It was for me and my friends. My parents didn’t know about it. Most people didn’t know about it. If you met someone who loved The State, they were cool. Doug was the first character with a catch phrase (that wasn’t Louie, “I wanna dip my balls in it” which was great in its own way). I’m outta heeeere was a simple catch phrase but I loved it. Plus, “Oh you mean Uncle Robert?” is one of the best sketch lines of all time.

Barry and Levon

This State sketch had “Sexual Healing” playing underneath it the whole time, so, it had to be dubbed again decades later and it’s just not the same. But in high school, it was the funniest most random thing I had ever seen. Two hundred and forty dollars worth of pudding. Good Lord why? But right from the start. “I’m Barry.” “And I’m Levon, Sagittarius.” I was dying laughing.

East/West Bowl

This sketch announced Key and Peele. I may have watched this sketch more than any other sketch on this list. It got funnier and funnier every time I watched it. Yeah, it spawned a bunch of sketches that weren’t as good and, at times, felt a little forced. But it’s a classic, no question.

Charlie Murphy’s True Hollywood Stories – Rick James

Much like Lazy Sunday, this sketch changed the game. The second it came out, people were saying, “Did you see the Rick James sketch?” Chappelle’s Show had a lot of brilliant sketches but this will always be the most important one. (Though, I have to say, for all of Dave Chappelle’s “Key and Peele stole my sketch show…” this format of someone telling a story and actors acting it out was done in MTV’s You Wrote It, You Watch It featuring actors that would go on to be on, you guessed it, The State.)