July 23, 2015: James and Paula Abdul recreate the "Opposites Attract" video, with James as MC Scat Kat.
Whenever James surprises/impresses one of his fellow passengers with his singing in the Carpool Karaoke segments. Not quite Hidden Depths, since he's appeared both on Broadway and in the Into the Woods movie (and hosted the Tonys), but it's definitely gratifying. Check out his, Nick Jonas, and Demi Lovato's harmonies when they sing "Jealous" a cappella.
In the Gwen Stefani installment, she tells him what she's singing during the fast patter part of "The Sweet Escape." When they start singing along again, James immediately nails it.
Similarly, in the Broadway installment the week before the Tony Awards, he delivered LaFayette's first verse from "Guns and Ships"almost perfectly. Granted, he did slip up on the second verse, but still, those are the fastest lines in the history of Broadway, and he did an impressive job holding his own.
The entire Michelle Obama/Missy Elliott ride is a huge Moment of Awesome, but special mention goes to James nailing a verse of "Get Ur Freak On" that neither Michelle nor Missy are shown to remember. Missy even gawks for a second when she sees how much he remembers.
At the 2016 Creative Arts Emmys, the show managed to win the prize for Best Interactive Program. Additionally, the Carpool Karaoke Prime Time Special won the award for Best Variety Special over things like Adele Live in New York City and Beyoncé's Lemonade.
"Spill Your Guts or Fill Your Guts" with Jimmy Kimmel. Jimmy happily eats everything placed in front of him (which he partially owes to smoking a joint beforehand). He even starts eating pig blood curd before James asks the first question!
The Christmas episode of Carpool Karaoke has Mariah Carey asking James to sing her hit, "All I Want for Christmas Is You". He obliges, and the rest of the video turns into an epic compilation of most of the previous CK guests singing the song, having recorded the material in their respective episodes. It's not only an awesome moment in itself, but the secrecy and planning behind it is doubly awesome.