Before I dive in, you must know that I’ve watched this endearing special at least once every year since it originally aired in 1988. For the first 20 years or so, it was viewed on my family’s copied-from-TV-to-VHS copy, all-inclusive with 80s holiday commercials. In my 20s, I got the DVD, and now I have the Blu-ray. Though, I still have a VHS-to-DVD copy kicking around—one I simply watch for the commercial breaks.
My fandom is strong and my knowledge is great—so, let’s get back to that ranking…
14. Oprah Winfrey. If it weren’t for Whoopi’s gaffe, Oprah would be the weakest guest. Her pace is totally off from Pee-wee’s, and she’s just awkward. Her only saving grace is her Pee-wee laugh. It’s flimsy, but at least she (kind of) tried.
13. Joan Rivers. The only thing lamer than appearing via picture phone is making your cameo appearance by way of Hollywood Squares on TV. Sorry, Joan—you may have been wearing a snazzy “Merry Christmas” sweater, but you also interrupted the cartoon segment.
12. Dinah Shore. The last of the picture-phone callers! Dinah edges out Oprah, Whoopi, and Joan because 1) she sings a song for Pee-wee (true, an annoying one); and 2) she manages to snag the show’s tag—when she finishes her 1,436 Days of Christmas song.
11. Zsa Zsa Gabor. Dahling, Zsa Zsa is totally forgettable. But at least, she’s there in person—appropriately hanging out with Cowntess.
10. Cher. Her appearance is brief, glittery, and pushes the story forward as she’s there for the secret word (YEAR). She and Pee-wee press Conky’s buttons, get the word, scream, chat—and then Cher’s on her merry way, but not before uttering YEAR one last time. MORE SCREAMS!
8. k.d. lang. “Jingle Bell Rock” is fun, holiday fare—so, k.d. lang has a grand, swinging time singing this tune, complete with a Christmas-y party dress and random laughing outbursts. Post-song, she shares a few rhymes with the Puppet Band. But, for the record, I still don’t know what she says at the end of her song—can anyone help a girl out here?
7. The Del Rubio Triplets (Eadie, Elena, and Milly). In case you haven’t noticed, songs are aces for me in this Christmas special—so, the De Rubio girls bring it threefold with “Winter Wonderland.” If you grew up in the ‘80s/’90s, chances are you know these sisters from their varied TV appearances—including The Golden Girls, Full House, and Night Court. Following my light research, I was sad to learn that all three have passed away. But it’s okay. With syndication, they live on. So, keep slaying those bells, ladies.
6. Frankie Avalon. He’s the lesser part of the still-great Frankie and Annette dual appearance. Pee-wee enlists the fictional couple’s help to make holiday cards. It becomes a craft moment (with toothbrushes and potatoes) and a running gag. They’re the only “celebrities” to appear all throughout the Christmas special—save for Dinah Shore, but again, that’s only on the picture phone. Still, Annette ranks higher—more on that in a moment.
5. Grace Jones. As luck would have it, Reba the Mail Lady mistakenly delivers one large crate to the Playhouse (vs. the White House). So, Grace Jones arrives on scene (out of the crate) and melodiously rules a rendition of “Little Drummer Boy” (second only to Joan Jett’s version). Bonus: She’s another guest star to have an impact on my child—he’ll wear my bra and say he’s Grace Jones. You can see why…
2. Magic Johnson. He’s Magic Screen’s COUSIN! As a kid, I thought this to be true. As an adult, I recognize its brilliance—even though Magic Screen and Magic Johnson only share first names and aren’t even of the same species/logic... whatever, it’s still my favorite line. And for this reason alone, MJ would be #1 if it weren’t for…
Now, rank your own—but if you’re an Oprah fan, kindly move along.