- Pee-wee: That was Cher! Cher was right over there! In the same room as my chair! I hope I didn't stare! Oh well! I don't care!
- Dinah Shore: [to the tune of "12 Days of Christmas"] On the 500th day of Christmas, my true love sent to me...
- Little Richard: You know what they say Pee-Wee, if at first you don't succeed, you get back up and you try... and you try... and you try it again... except ice skating, I give up, I quit!
- Pee-wee: Now I'm going to make an angel in the snow. If you don't have snow at home, just use 20 pounds of coconut shavings!
- Dinah Shore: [to the tune of "12 Days of Christmas"] ... 20 pounds of fruitcake, 19 CD players, 18 bags of nachos, 17 body builders...
- Whoopi Goldberg: Hi, Pee-wee, Merry Christmas. I was just wondering if I could be on your Christmas special.
- Pee-wee: I'm awfully sorry, Whoopi, but I've already booked too many stars as it is.
- Whoopi Goldberg: Oh. Well, how about next Christmas?
- Pee-wee: Next year's special is already booked too. I might be able to squeeze you into the Christmas special two years from now.
- Whoopi Goldberg: Two years from now? Oh, okay. That's alright. Would you do that?
- Pee-wee: I'm not promising you anything now, Whoopi.
- Cowboy Curtis: You know, Pee-Wee, they say if you stare at a snowman long enough, it'll come to life.
- Snowman: Why don't you take a picture? It'll last longer.
- Little Richard: If God had wanted me to ice skate I would have been born with skinny feet and a little head.
- Floory: Hey Miss Yvonne, come stand over me!
- Grace Jones: [Grace Jones, stepping out of a large wooden crate that she was "delivered" to the playhouse in, and giving Pee Wee a confused stare] You're not the president... you're Pee Wee Herman.
- Reba: [Inspecting the wooden crate] This package was supposed to go to the White House, not the playhouse.
- Ms. Yvonne: Aren't you going to comment on my hair?
- Pee-wee: Wow! Christmasy! But what's the plant growin' out of it?
- Ms. Yvonne: It's mistletoe! You're always supposed to kiss somebody if they're standing underneath the mistletoe! This way, I'm assured hundreds and hundreds of kisses from everyone!
- Pterri: Stand over here.
- Chairry: Stand over here!
- The Fish: Come over here and give us a big, wet kiss!
- Ms. Yvonne: Oh, don't worry. There's enough of me for everybody!
- Pee-wee: [guiding everyone in Christmas carols] Deck-the-Halls!
- Everybody: Deck the Halls with Boughs of Holly/Fa la la la la, la-la la la...
- Pee-wee: Sleigh bells!
- Everybody: Sleigh bells ring, are you listening...
- Pee-wee: No, No! Sleigh bells! On the roof! Do you know what that means?
- Reba: You've had too much eggnog?
- Pee-wee: No, get out the milk and cookies! Hurry!
- Pee-wee: The stockings were hung by the chimney with care, and I hope everything on my list will be there.
- Pee-wee: Excuse me, Miss Yvonne, but before you go making out with everybody in the playhouse, how about forking over that gift?
- Pee-wee: Hi, Magic, what are you doing inside the Magic Screen?
- Magic Johnson: The Magic Screen and I are cousins.
- Frankie Avalon: Pee-Wee, we've finished the Christmas cards.
- Annette Funicello: Exactly 1,000.
- Pee-wee: Ooh, let me count them. Ha ha, just kidding. Now you can start making the envelopes.
- King Of Cartoons: Guess what I've got for you, Pee-Wee?
- Pee-wee: It's not a fruit cake, is it?
- King Of Cartoons: No, of course not. It's two fruit cakes.
- Pee-wee: [Dictating Christmas list] Alright, Conky, "In conclusion, add to that a pup tent, football, new train set, seven encyclopedias and one of those dolls you fill up with the gooey-gloopy stuff." Sign it, um, "Most sincerely yours - especially on this holiday season - Your Pal, who's been very, very, very, very, very good all this whole year long, Pee-Wee 'I'm not kidding about how good I've been' Herman. P.S., I really have been good. Please believe me, Santa, please! Please and thank you. I've practically been an angel".
- Conky: Gee-gee-gee, Pee-Wee, do you think you asked for enough?
- Pee-wee: Hmm, no. But I didn't want to appear to be greedy. Print that out, would you, Conky?
- [When the list is printed, it is several miles long]
- Randy: There ain't no such thing as Santa Claus.
- Pee-wee: Alright, I'll just take your stocking down.
- Randy: Wait a minute, Pee-Wee, let's not be hasty here. Why not leave it up? Just for decoration, you understand.