This Christmas, let’s revisit two of Justin Timberlake’s iconic holiday-themed moments on Saturday Night Live! These sketches have become fan favorites, combining Timberlake’s comedic timing, musical talents, and festive cheer.

Dick in a Box – SNL Digital Short (Season 32)

A tongue-in-cheek homage to the sultry R&B ballads of the 1990s, Justin Timberlake joined forces with Andy Samberg in this unforgettable Saturday Night Live digital short. Playing a pair of wannabe R&B crooners, the duo hilariously serenades their girlfriends—portrayed by Kristen Wiig and Maya Rudolph—with their “creative” holiday gifts. This bold and hilarious performance struck a chord with audiences and even earned Timberlake a Creative Arts Emmy for Outstanding Music & Lyrics in 2007.

Bring It on Down to Wrappinville – SNL (Season 39)

Justin Timberlake and Jimmy Fallon team up as Christmas wrapping store reps in this laugh-out-loud Saturday Night Live sketch. Dressed as a roll of wrapping paper and a holiday gift bag, the duo uses clever rhymes to attract customers. But their holiday hustle faces some competition from a rival vendor, hilariously played by Aidy Bryant. The result is a festive showdown packed with laughs, creativity, and plenty of holiday cheer.

These sketches are perfect for adding some humor and holiday spirit to your day. Merry Christmas and Happy Holidays from Justin-Timberlake.org!

Andy Samberg, Bring It on Down to Wrappinville, Dick in a Box, Jimmy Fallon, Justin Timberlake, Saturday Night Live