One of the highlights of “Saturday Night Live” since 2006 was seeing a black screen with the words “An SNL Digital Short.” The Lonely Island gang produced some of the most memorable moments in the history of the show. It’s understandable why they’ve received hundreds of millions of views. Here’s a look at the 25 greatest digital shorts of all time.
25. Pep Talk
Fred Armisen plays a fast food manager who attempts to give his employees a pep talk but struggles to hold in his explosive anger when Bill Hader’s character shows up late. Matthew Fox is hilarious as he tries to help his boss get on the right track, which only makes Armisen more angry.
24. Business Meeting
Rainn Wilson guest stars as a corporate executive trying to come up with a way to save a struggling company, but the employees that he asks for advice keep getting more and more bizarre. At one point a giant turkey sandwich offers advice. Eventually the executive gets a phone call letting him know the building is about to be blown up and everyone dies.
23. Andy’s Dad
Jonah Hill confronts Andy Samberg and confesses that he is in love with Andy’s father, Ben, who is played by the fantastic Jim Downey. Soon after, Bill Hader enters to declare his love for Ben as well.
22. Giraffes!
Jason Sudeikis portrays the head of the Staten Island Zoo and presents a video that students created about giraffes. Little does he know that the video is actually about how giraffes can shoot lasers and are trying to destroy humanity.
21. Threw It On The Ground
Samberg plays a beatnik who gives a poetry slam about fighting corporations and conformity by throwing various items on the ground. It ends with Ryan Reynolds and Elijah Woods chasing him down and using a taser on his butthole.
20. Dear Sister
This is one of the most bizarre and controversial shorts, as it was pulled due to the timing of its airing coinciding with the Virginia Tech shooting, while containing several scenes that feature gun violence. The whole thing is a parody of an episode of “The O.C”. and is set to Imogen Heap’s song “Hide and Seek.”
19. Like a Boss
Seth Rogen guest stars as a company evaluator interviewing Samberg about what he does on a day-to-day basis. The rap starts out with average, normal managerial duties, but quickly turns into bizarre encounters with giant sewer fish and chopping off his genitals.
18. Flags of the World
In this short, Samberg raps about the flags of the world, but quickly starts singing about fictitious flags including the “We Love Betty White” flag. I’m no geography teacher but I’m fairly certain that’s not a real place.
17. Rescue Dogs 3-D App
Samberg tries to call 911 when he hears burglars enter his home, but the app keeps flooding him with pop-ups for a movie called Rescue Dogs 3-D. He’s eventually saved when Resuce Dog shows up to take care of the robbers.
16. Party Guys
Samberg and Bill Hader attend a party when everyone is a literal representation of slang terms. There is a group they refer to as “sons of bitches,” which is revealed to be a litter of puppies while a group of “jokers” are dressed a The Joker from the Batman series.
15. Great Day
In this Disney-like musical, Samberg plays a cocaine addict on a drug binge singing about how great of a day he is having. The song gets faster and faster as he does more and more drugs and begins to hallucinate in a more extreme manner.
14. The Creep
This is probably the only time you’ll see John Waters and Nicki Minaj in the same video. The gang dresses as creepy older guys and raps about a new dance known as The Creep. As weird as it is, it’s surprisingly catchy.
13. Iran So Far Way
Andy Samberg and Adam Levine declare their love for Mahmoud Ahmadinejad, played by Fred Armisen, after Mahmoud declared there were no gays in Iran. The cameo by Jake Gyllenhaal is beyond perfect as well.
12. Jizz in My Pants
The song went on to be the first single on The Loney Island’s debut album, “Incredibad,” but started out as an absolutely hysterical digital short that featured Samberg and Akiva Schaffer singing about premature ejaculation caused by everything from attractive girls to the ending of “The Sixth Sense.”
11. Shy Ronnie
Rihanna and Samberg, who portrays a nerdy loner named Shy Ronnie, perform a song for a classroom of children, but every time Rihanna tries to turn the song over to Ronnie, he mumbles and freezes up. The song was actually nominated for an Emmy for outstanding music.
10. I Just Had Sex
Akon joins the Lonely Island in singing about having subpar sex with gorgeous women, all the time thinking it was the greatest experience of their lives. The short also features Blake Lively and Jessica Alba as the not-too-thrilled recipients of the awful sex.
9. 3-Way (The Golden Rule)
This is the third short featuring Timberlake and Samberg as the same characters, this time they’re both joining Lady Gaga in a night of sex while explaining that it isn’t gay as long as there’s a female involved.
8. I’m on a Boat
Andy Samberg wins a boat trip from a cereal box and decides to take Akiva and T-Pain along with him, completely ignoring his other friend Jorma. The trio then give a hardcore, profane rap about the joys of riding around on a boat.
7. Laser Cats!
In one of the most popular recurring digital shorts, Bill Hader and Andy Samberg come into Lorne Michaels office trying to pitch him a low budget movie where the two play super heroes that use cats to fight evil since cats can now shoot lasers.
6. Natalie’s Rap
During an interview, Natalie Portman, who is known as clean-cut and well-educated, breaks into a hardcore rap that ends with her breaking a chair over Chris Parnell’s back.
5. Mother Lover
Samberg and Timberlake are released from prison five months after the events of “Dick in a Box” and decide to give their moms, played by Susan Sarandon and Patricia Clarkson, the ultimate Mother’s Day gift by having sex with them. They’ll have sex with each other’s mom, not with their own.
4. United Way
Peyton Manning shocked everyone when he did this short about him mentoring kids in the most horrific way possible. He yells and screams at them while teaching them how to steal a car. It’s amazing.
3. Lazy Sunday
Andy Samberg and Chris Parnell give one of the most memorable performances ever on the show as they rap about spending a Sunday going around town on their way to watch “The Chronicles of Narnia.”
2. Dick in a Box
Justin Timberlake and Andy Samberg give a sexy’ 90s style R&B ballad about giving the ultimate Christmas gift. As ridiculous as the title is, good luck not having the song stuck in your head for a week after hearing it.
1. Jack Sparrow
Not only does this short feature Michael Bolton, but it features a Michael Bolton who is so obsessed with “Pirates of the Caribbean” that he keeps getting sidetracked during the song and proclaiming his love for the movie and Captain Jack. Watch it in all of its glory below.
