- March 31, 1999: Bear of Bear in the Big Blue House. Also in the episode are Cheech Marin, Alexandra Paul and foot products.
- December 1999: Bear of Bear in the Big Blue House makes a holiday visit and teaches Donny and Marie "The Bear Cha-Cha-Cha." The segment is in promotion of the video A Berry Bear Christmas. According to Noel MacNeal in a Tough Pigs interview, the kissing on the nose Bear got from Marie Osmond was not planned, and had gotten the puppet wrangler worried about the lipstick ever coming off his nose.
- May 25, 2000: Elmo appears; this may be one of the two appearances below, or an entirely different third appearance. Other guests are Susan Sullivan, Danny Bonaduce, and John Dye.
- Donny sings "Anything You Can Do" with Elmo. They talk about season 31, and Marie brings out brussell sprouts, the only food Elmo doesn't like. Aired outtakes reveal Marie had trouble singing "A, You're Adorable".
- In the above segment, Marie references the previous appearance.