From Laser Cats to Lazy Sundays, Captain Jack Sparrow to Michael Bolton on a boat, Timothée Chalamet and his Tiny Horse, and Natalie Portman passionately rapping profanity and sexually charged lyrics, Saturday Night Live Digital Shorts have been a fan favorite for years. Andy Samberg arguably ushered in the trend with his comedy group The Lonely Island and their parody music videos and songs.
They became so popular that some of the songs topped the charts after the Shorts introduced them. The torch was passed to Pete Davidson, who became popular for starring in many Digital Shorts during his time as a cast member. In the current season, the writing team behind the latest Digital Shorts is known as Please Do Not Destroy, putting their fresh take on the trend.
Whether classic or relatively new Digital Shorts, fans of the long-running comedy sketch series often gravitate to a mix of their favorites. These three SNL Digital Shorts are ones you should watch right now. Once you’re done, check out our lists of the 10 funniest SNL skits ever.
D**k In A Box (Season 32, 2006)
It’s a classic SNL Digital Short, but one that never gets old. Not surprisingly, it always resurfaces around the holiday season. Featuring a song written by Samberg and The Lonely Island, it features Samberg with pop star Justin Timberlake dressed like ‘90s boy banders (most comparable to the members from Color Me Badd). Along with the suits and bright-colored shirts is a gift-wrapped present positioned strategically overtop each of their netherregions. The raunchy ballad is about their thoughtful gift (you can take a wild guess what it is) in the style of an over-the-top mock music video. The lucky ladies receiving the presents are their female lovers, played by Maya Rudolph and Kristen Wiig. They nail the roles of the typical ‘90s music video female being wooed.
It’s not just the song and lyrics itself that make D**k In a Box a must-watch, it’s how committed the two men are to the performances. If you weren’t listening to the lyrics, you might think this was a real ‘90s music video featuring two overly expressive heartthrob musicians. Not surprisingly, D**k In A Box became a viral hit sensation, garnering millions of views on YouTube and counting. It is widely considered to be one of the best Christmas-themed Digital Shorts in SNL history.
Stu (Season 46, 2020)
Another Christmas-themed sketch, Stu features Pete Davidson playing the title character, a parody of the fictional character Stan from the Eminem song and music video of the same name. In the tragic song, an obsessed fan repeatedly sends letters to Eminem, getting increasingly frustrated that he isn’t getting a reply. His words get more violent and angry as time goes on, his voice and actions matching the intensity with each one. By the end, the man has sadly died by suicide before Eminem finally gets a chance to reply.
SNL and Davidson take the sad but fictional story and, as is customary for the sketch comedy show, make it humorous. In this version, Stu is passionately penning a letter to Santa (played by Jason Bateman in an intro sketch to the Digital Short), singing the rap as he vigorously writes down his wishes. What does he want? He’s desperate for a Sony PS5 which, at the time the episode aired, was the most coveted gift and the most difficult to find. The best part of the Digital Short, aside from the Elton John impersonation for the remixed bridge, comes at the end when Eminem himself makes a brief cameo appearance.
United Way (Season 32, 2007)
Also from season 32, fans laughed hysterically at Peyton Manning’s Digital Short about volunteering with a youth group for the United Way. It’s supposed to be a PSA for the organization and all the great work that Manning does, but it ends up depicting him as a horrible person. He screams at the kids, insults them, reads gossip magazines to them, teaches them how to break into cars, and even gets them tattoos. It might not otherwise be funny, but because the Short is so over-the-top and Manning has such a squeaky clean image, it’s brilliant.
The laughs come immediately when Manning turns ugly and pegs a kid in the face with the football, which sets the tone for the hilarity to come. “Get your head out of your ass!” he yells to the child who misses the catch. “You suck!” The behavior is so out of character for Manning but his convincing acting makes the Short an unexpected treat and a fan favorite.
