The whole ending of Muppets Celebrate Jim Henson. What I always do when that scene is on, I pretend it's still 1990. I watch the scene, get teared up over those beautiful letters ("We will miss you, Jim Henson. Matt." - Robin), then that wonderful song, and all of a sudden - there's KERMIT! Jim died, but there is Kermit! And then the unexpected happens - Kermit TALKS! And everything is sortta back to normal again!
A lot of the songs on Jim Henson: A Sesame Street Celebration. Especially the three Kermit songs at the end: Frogs in the Glen, The World Above, and This Frog. You definitely have to hear them in this context, in this order, at the end of the album.
Rowlf singing Old Dog Trey on Ol' Brown Ears is Back. Can you imagine ol' Rowlf playing the piano on that large stage, howling his doggy lungs out over his lost dog friend? They completely hammed up the TMS version BTW.
Gonzo's version of My Way, and how Kermit reacts to it.
The Muppet Family Christmas Carol Singing at the end. That made me cry when I was six and saw it for the first time.
Same goes for Gonzo's Wishing Song when he plans to marry guest star Madeline Kahn, but she confesses she just wanted to make a compliment to him.
Scooter and John Denver singing The Peace Carol.
Mew being frozen forever in The Christmas Toy.
Kermit in the Muppet Movie: "Go ahead and kill me." Doc Hopper: "Alright boys. Kill him." Look at the reactions on the Muppets' faces.
Frank crying over the loss of Jim in People's Profiles.
Every time clips of Jim Henson are shown while The Rainbow Connection is playing.
Gonzo saying goodbye in MFS.
Saying Goodbye from MTM.
Mr. Hooper's death.