Viewing Stephen Colbert’s hilarious special with musical guests like Elvis Costello, Feist, Toby Keith and John Legend again got us thinking though.

The coolest musical pairing on a holiday special is probably hands down David Bowie and Bing Crosby’s “Little Drummer Boy.” But what’s the most awkward, inappropriate, unintentionally hysterical or just plain weird one?

Grace Jones arriving in a giant crate wearing what looks like a placemat on her head on the “Pee-Wee’s Playhouse” Christmas show comes to mind. It’s either brilliant or very, very strange.


Friday, December 12
Barry Manilow – “The Ellen DeGeneres Show”
Randy Sklar, Jason Sklar – “Chelsea Lately”
Tony Bennett – “The Hour with George Stroumboulopoulos”
REO Speedwagon – “The Bonnie Hunt Show”
Jeff Altman – “Late Show with David Letterman”
Jamie Foxx – “The Tonight Show with Jay Leno”
Don Rickles, Erran Baron Cohen – “Late Night with Conan O’Brien”
Barry Manilow – “Jimmy Kimmel Live!”
Kathy Griffin – “Last Call with Carson Daly” – rerun

Saturday, December 13
Brian McKnight – “The Early Show”
Crowded House – “Austin City Limits” – rerun
Kanye West – “Saturday Night Live”

Monday, December 15
John Legend – “The View”
Ludacris, John Caparulo, Natasha Leggero, Jo Koy – “Chelsea Lately”
Adam Sandler – “Late Show with David Letterman”
Dame Edna, Sheryl Crow – “The Tonight Show with Jay Leno”
Eddie Izzard, John Legend –“Late Night with Conan O’Brien”
Lady GaGa – “Jimmy Kimmel Live!” – rerun