Songfacts®:

• In this song, Justin Timberlake and Andy Samberg present their ladies with a special gift for the holidays: a dick in a box. They even give step-by-step instructions on how to pull it off (Step 1: Cut a hole in the box, Step 2: Put your junk in that box).
  
  It first aired on the December 16, 2006 episode of Saturday Night Live as a Digital Short and quickly spread around the internet, becoming one of the most famous skits in the history of the show.
• The charm here is in the delivery: these guys really seem to believe they've found the perfect gift. And musically, it's authentic, sounding like an early '90s hit from Color Me Badd.
  
  Justin Timberlake was the perfect guy to pull this off. Dating back to his 'N Sync days, he could sing any lyric with conviction, a talent he could alchemize into comedy gold. He was a Saturday Night Live favorite, often appearing as a host and/or musical guest, with memorable appearances impersonating Robin Gibb and as an overqualified mascot.
• SNL Digital Shorts were the creation of cast member Andy Samberg and the writers Akiva Schaffer and Jorma Taccone. They went to high school together in Berkeley, California, and after college they got together as a comedy collective called The Lonely Island. Pre-YouTube, they make quirky, low-budget videos and posted them on their website. Saturday Night Live hired them in 2005, and that season they had a breakout with "Lazy Sunday," one of the first videos to go viral on YouTube, which launched earlier that year. Empowered with bigger budgets and more airtime, they kept the Shorts coming, and started attracting celebrities, starting with Natalie Portman, who starred in "Natalie's Rap" later that season.
  
  "Dick In A Box" came in The Lonely Island's second season on the show. By this time, their Digital Shorts were the showstoppers, and getting someone like Justin Timberlake on board was an easy sell. NBC posted the videos on nbc.com and they showed up all over YouTube. The YouTube versions would often get taken down and reposted until NBC put it up on their official channel in 2018.
  
  The Lonely Island managed to retain their self-effacing humor and underdog attitude. In 2009, they included "Dick In A Box" on their first album release, Incredibad.
• The song started out as a parody of '90s R&B boy bands, particularly the kind with at least one white member, like All-4-One and Rythm Syndicate. Once the track was built in that style, The Lonely Island came up with the storyline, which made it much more than a genre parody. Setting it in the '90s worked really well visually, giving Timberlake and Samberg an excuse to wear ill-fitting suits, cheesy sunglasses and gold chains, all while rocking ridiculous goatee-beards. And although Timberlake was more than capable of busting a move, he made sure not to, acting like he was struggling to keep up with the rudimentary choreography - another staple of the groups they were making fun of.
• Like many of the best SNL skits, "Dick In A Box" was made in less than a week. The Tuesday before the show, The Lonely Island asked Katreese Barnes, who worked on music for the show, to come up with a track in the style of the '90s R&B groups they wanted to make fun of. That Thursday, the concept came together and they wrote the song with Timberlake, who was both the host and musical guest that week. They spend most of Friday shooting the video (with cast members Maya Rudolph and Kristen Wiig as the girlfriends), which aired the next day on the show.
• It seems quaint, but Saturday Night Live had to bleep out the word "dick" when this aired, per FCC guidelines. That's because they're a broadcast network, which is on a much shorter leash than a cable network or streaming service. The bleeps seemed to make it even funnier; NBC posted both censored and uncensored versions on their website, but when they put it on their official YouTube channel in 2018, they left in the bleeps.
• Lady Gaga took the Justin Timberlake part in "Dick In A Box" for the 2025 SNL50: The Homecoming Concert special, which kicked off a medley of Lonely Island classics. The bit started with Samberg trying to sing her hit "Shallow," but failing miserably.