Ranking Every Friend in Pee-wee’s Big Adventure From Worst to Best

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It’s the 30th anniversary of one of the greatest comedies of all time, and we’re celebrating by ranking every single one of Pee-wee Herman’s memorable friends in the classic film!

Hi all! Dave here. Thanks to the generosity of our Patreon supporters, we’ve been able to make a regular feature out of arbitrary rankings like every fighter in Bloodsport and every skit in The Simpsons’ “22 Short Films About Springfield.”. With the 30th anniversary of Pee-wee’s Big Adventure, I’m celebrating my all-time favorite comedy film by ranking every single one of Pee-wee’s friends in said movie. Sorry, Pee-wee’s Playhouse fans, I’ll save the rankings for those characters for another day (SPOILER: The King of Cartoons is the best).

A few ground rules before the list commences. Large groups are consolidated into one spot (I don’t know if any of Satan’s Helpers have names), characters have to have had a meaning interaction with Pee-wee DURING the adventure (Hobo Jack’s friends don’t count, nor does Simone’s new boyfriend), and there has to be proof of friendship, not just false claims.

SORRY BUX...TON
SORRY BUX…TON

With those regulations out of the way, lets get onto the rankings!

amazinglarry

18 – AMAZING LARRY

This is bending the rules a bit, since there’s no real interaction between Pee-wee and Larry besides Pee’s admonishment, but since everyone else at the impromptu meeting was a friend, I’m counting it. However, Larry’s lack of tact during said meeting shows his lack of consideration as a friend.

terry

17 – TERRY

This guy suffers from a lack of screen time, showing up as a deus ex machina to keep Pee-wee from getting punished. Also, was this guy using Pee-wee just to profit off his story? Anywho, Pee-wee liked being called “babe,” so that keeps Terry from the cellar.

bmxkids

16 – BMX KIDS

Don’t get me wrong, these kids are indeed radical, but I worry about their influence on Pee-wee. For all of tricks he utilized to escape with his bike, Pee-wee subjected himself to a lot of risks and injury to win their favor.

berle

15 – MILTON BERLE

Haha, duck. Berle didn’t eject Pee-wee from his crew after noticing his laughter, so that’s friendly enough to rank near the bottom of this list.

largemarge

14 – LARGE MARGE

Another technicality. Sure, Pee-wee was scared of this apparition, but she told him a story and probably meant well when she passed along the “Large Marge sentchya” phrase. I bet it would have been worth a free coffee back when LM was alive and well!

platformshoes

13 – PLATFORM SHOES GUY

Of all of the selfless gestures others make for Pee-wee over the course of the film, this one meant the most. Before he got those magic shoes, Pee-wee was scheduled to be raped, stomped tattooed, hanged, and then killed, so this was a pretty important favor.

satanshelpers

12 – SATAN’S HELPERS

These guys (and gal) start out pretty antagonistic with Pee-wee, and their favor of lending him a motorcycle leads to his hospitalization, but in between those calamities they’re pretty nice to him.

hobojack

11 – HOBO JACK

No, not Bojack (we ranked all of the Bojack Horseman characters in another list, by the way), though this guy is just as oblivious. Out of all of the friends Pee-wee makes during his travels, Jack is the only one who manages to annoy the titular character. However, Pee-wee probably went through the most trouble to track Jack down for the premiere, so there’s has to be some level of friendship.

Find out where Mickey and Dottie rank on the next page!

7 thoughts on “Ranking Every Friend in Pee-wee’s Big Adventure From Worst to Best

  1. The only thing I disagree with is that Amazing Larry should be #1. I haven’t been so interested in a minor character’s backstory since Boba Fett! And with zero evidence whatsoever, I’m going to confirm he was the basis for Lemmy Koopa.

  2. Excellent list, though it made me realize that none of the regulars from Pee-Wee’s Playhouse show up in the film. Granted, the film is perfection and it was doing its own thing, but it would have been nice for Laurence Fishburne to at least show up in a cameo.

    Also, awesome fun fact I learned just today: The lady from the Satan’s Helpers gang? That’s Elvira! Cassandra freaking Peterson! This leads me to a possible LT episode suggestion: Actors in unrecognizable roles or cameos. I’m drawing a blank for other examples right now, except maybe Tom Cruise in Tropic Thunder.

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