Today marks the 61st birthday of actor Paul Reubens, best known to the world as Pee-wee Herman. Although he took an extended hiatus from his most beloved character following for nearly two full decades following his 1991 arrest, Reubens has been regularly making the rounds over the past few years as the guy who demonstrated supreme swag in his suit and tie before Justin Timberlake was born.
To commemorate his birthday, here are the top five funniest Pee-wee Herman moments since his 2009 return.
5. CNN Interview with Alan Duke (2009)
It seems like it takes Pee-wee a few minutes to figure out whether or not Duke is serious in his interview, and the tension is glorious to watch. Duke asks Pee-wee whether or not he supports “play marriage,” since the tagline for the 2010 Los Angeles run of The Pee-wee Herman Show was “The new stage show you’ll love so much you should marry it!,” and that’s just in the first minute. For a major news outlet, this ranks as one of cable television’s most bizarre interviews, for sure.
4. Pee-wee and Conan O’Brien Explain Ash Wednesday (2010)
There have been a number of memorable Pee-wee appearances with Conan, but this one might be the best. Dressed like an angel at a school pageant, Pee-wee, along with Conan and the rest his late-night team, explain quasi-accurately what Ash Wednesday is. Look out for the appearance of the giant steak and can of tuna!
3. The Pee-wee Herman Show on Broadway (2011)
By far, the biggest achievement of Pee-wee’s recent return, and easily one of the biggest accomplishments of his decades-long career, was the HBO broadcast of his Broadway show. The playhouse was completely recreated on stage, staying true to Gary Panter’s original design for Pee-wee’s Playhouse. A decent portion of the script was lifted from the 1981 run of The Pee-wee Herman Show that launched the character into the stratosphere. Original cast members like Lynne Marie Stewart (Miss Yvonne), John Paragon (Jambi the Genie), and John Moody (Mailman Mike) reprised the roles they created thirty years earlier. Simply put, this was a treat for fans – and pretty darned funny!
2. Pee-wee Gets an iPad (2010)
Filmed during the Los Angeles run of his recent stage show, this was Pee-wee’s first foray back into the mainstream in a big way. The Funny or Die video quickly went viral, and today has over 1.2 million hits on YouTube alone. Several of the Playhouse characters are here, but the real treat is how the video subtly, but hilariously, mocks modern technology. It’s a great blend of adult humor that at a first glance seems family-friendly, a format where the Pee-wee character is always at his best. After all, when else can you explain to hear a perfectly logical explanation of what a sanitary napkin is? (Spoiler alert! According to Pee-wee, it’s “a napkin that’s super-clean.” Of course it is.)
It’s completely plausible that more people saw Pee-wee Herman slamming shots, smacking Anderson Cooper over the head, and being treated to a cable television-style intervention with the cast of Saturday Night Live and several Playhouse characters than any other appearance since his 1991 surprise appearance at the MTV VMA Video Music Awards. With adult humor, mild profanity, and even a recreation of his Pee-wee’s Big Adventure dance to “Tequila” on top of a bar, this is a clip that shouldn’t be missed. If and when there are future Pee-wee Herman projects, here’s hoping they are of a style and tone similar to this one.
Caseen Gaines is the author of Inside Pee-wee’s Playhouse: The Untold, Unauthorized, and Unpredictable Story of a Pop Phenomenon. His new book, A Christmas Story: Behind the Scenes of a Holiday Classic, will be released this October.