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