The Montclaires is a sketch written and directed by Trevor Moore. It features The Montclaires, a fictional 50's era group made up of jazz singers. The sketch was uploaded to YouTube on Christmas Eve 2006.
The Montclaires perform their songs I'm Not Driving You Home and When You Hit Your Woman at a club on Christmas 1959.
- Comedian Kristen Schaal plays the girl who gets slapped by Billy and Scotch.
- Blackie Jones is played by comedian Baron Vaughn, who appears in the Season 4 sketch Juror.
- Jenny Slate plays the 14 year-old who gets waved off by Billy. She appears in the Season 2 sketch Air Dry.
- The name of Trevor's character, Billy Sunday, is a reference to singer Billie Holiday.
- The Montclaires themselves are similar to the Rat Pack, a group of American entertainers popular through the 60's. Billy Sunday's constant poking fun at Blackie Jones' race is similar to how Sammy Davis Jr. was treated as a member of the Rat Pack. The Rat Pack was also known for their heavy drinking.
- Sam plays the security guard who carries Kristen Schaal's character away.
- The Montclaires' name is a reference to the town Trevor was born in - Montclair, New Jersey. There was also a 70's soul group named The Montclairs.