The Best Saturday Night Live Digital Shorts From The Samberg Era

Saturday Night Live has long been known for its monologues, fake commercials, and sketches. But Andy Samberg and his goofy friends from The Lonely Island changed the game when they introduced digital shorts back in 2005. In honor of his birthday, here are the best Samberg-era SNL digital shorts.

Andy Samberg

Image via Getty/Bravo

Andy Samberg

When we first met Andy Samberg back in 2005, he was a newly featured player on Saturday Night Live with, to be honest, a slew of bad impressions. But Samberg proved to be one of the freshest and, frankly, oddest voices during his tenure on SNL, and became one of the most beloved cast members in the show’s history. Extending his niche comedy into films like Hot Rod and his sitcom role in Brooklyn Nine-Nine, Andy has stayed on top since we first laid eyes on that perfectly geometric jaw.

Some of Samberg’s most notable work has been with his equally creative and funny friends Akiva Schaffer and Jorma Taccone. Known for their work as the comedy group The Lonely Island, the trio have certainly made a name for themselves as comedic musicians, writing fake raps and pop songs, often about extremely niche or mundane subjects. Their hyper-specific sense of humor paired with their keen social awareness skyrocketed their success as a comedy troupe, with three studio albums and even a movie in their classic parody style. Real hype for The Lonely Island resurfaced when they performed their first live concert at Clusterfest in June, but some of their most infamous work came during Samberg’s time as a cast member on Saturday Night Live while Schaffer and Taccone served as writers.

After 43 years on air, SNL has gifted us with innumerable moments that have evolved into cultural relics. But none compare to the digital shorts introduced in 2005. Generally written and directed by the boys from The Lonely Island, the digital shorts quickly became a fan-favorite segment of the show. Though they still occur regularly, the Samberg era of digital shorts was undeniably iconic. In honor of Samberg’s 40th birthday, we’re taking a look back at some of his best SNL digital shorts. Me likey dat.

15. "Great Day"

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Original Air: May 15, 2010

For an upbeat musical number, “Great Day” is actually kind of dark. Regardless, watching a sad, coked-up businessman perform a full on Disney-esque musical bit has great entertainment value. Some of the best digital short moments are the most unexpected, i.e. watching Samberg lose his shit when people touch him and turn into a demon for a split second.

14. "Space Olympics"

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Original Air: Sept. 13, 2008

This short is about an alien who, as the title suggests, hosts the Olympics in space. It’s by far one of the weirdest digital shorts, but the concept of the games slowly falling apart piece-by-piece because of the recklessness of hosting a sporting event in space is *chef’s kiss.* Whether Samberg is serenading us with words of encouragement or accidentally pressing the self-destruct button and fighting off alien intruders, this short deserves a gold medal.

13. "Jizz In My Pants"

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Original Air: Dec. 6, 2008

It’s not just the objectively good music and falsetto bridge that make “Jizz In My Pants” one of the best shorts—it’s the fact that it feels more like a Lonely Island music video that happened to make it on TV. The off-brand British pop personas taken on by Samberg and Taccone are spot on, and the repeated joke that literally everything makes them, uh, jizz in their pants, is just juvenile enough to work for two and a half minutes straight. Simple, but effective.

12. "Threw It on The Ground"

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Original Air: Oct. 3, 2009

When you really think about it, “Threw It on The Ground” is the protest song of the decade. The song revolves around ignoring the generosity of others by throwing their offerings on the ground, and Samberg somehow managed to find a character perfectly suited for such an uninvolved concept. He flawlessly portrayed an anti-conformist beatnik performing at some sort of poetry slam, and cameos from Ryan Reynolds and Elijah Wood that lead to Samberg getting his ass tased create the quintessential digital short twist ending.

11. "Laser Cats" Series

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Original Air: April 15, 2006

We cannot, in good conscience, include all seven parts of the “Laser Cats” series on this list, as it would be unfair to the other 99 digital shorts; we can, however, include them all in one ranking. Each episode starts with Samberg and fellow SNL alum Bill Hader pitching their homemade movie to Lorne Michaels, the mastermind behind Saturday Night Live. Each episode ends with Lorne kicking two doofuses out of his office for wasting his time with a poorly produced video of them playing with cats, both real and stuffed, and somehow involving incredibly successful actors and directors in their antics. Sigourney Weaver, James Cameron, Steve Martin, and even Steven Spielberg appeared in “Laser Cats” shorts, but the outcome was always the same: Samberg and Hader leaving Michaels office, only to return again next season with another half-assed attempt at their low-budget sci-fi film.

10. "Dick in a Box"

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Original Air: Dec. 16, 2006

The first single from The Lonely Island’s debut album Incredibad, “Dick in a Box” is one of the most well-known digital shorts ever made, and for good reason. It was specifically written at the request of Lorne Michaels to showcase Justin Timberlake’s voice, as he was the host and musical guest when the short aired. The short follows two ‘90s R&B-style musicians who give their lovers the ultimate Christmas package. Though the original airing censored the word “dick” 16 times, the short earned a Creative Arts Primetime Emmy for Outstanding Music & Lyrics in 2007 and led to sequels featuring the same characters. It embodies exactly what the digital shorts were originally about,: using a specific genre of music to depict a seriously obscure and ridiculous concept.

9. "I Just Had Sex"

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Original Air: Dec. 18, 2006

This slightly self-deprecating, somewhat humble brag of a song is another digital short classic that originally aired on SNL, but was ultimately a product of The Lonely Island’s musical endeavors. “I Just Had Sex” is by far one of the catchiest songs we heard in a short and celebrated getting laid, even if it wasn’t that good. Akon joined Andy and Jorma on the track with a melodic hook that had people everywhere singing and praising their sexcapades. It’s nothing short of a sex-positive anthem.

8. "United Way"

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Original Air: Mar. 24, 2007

One of the rare digital shorts that didn’t involve a musical parody was “United Way,” starring football legend Peyton Manning as the world’s worst mentor to young children. Mocking the PSAs that Manning did in the early 2000s for United Way Worldwide, this short features him pegging little kids with footballs before teaching them how to break into a car and using them to pick up women at the park. Taking someone as pure as Manning and depicting him as a dramatically negligent counselor to America’s youth fits perfectly into the digital short universe. 

7. "I’m On A Boat"

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Original Air: Feb. 7, 2009

Another example of The Lonely Island’s drastic approach to a mundane concept, “I’m On A Boat” is literally a song about Samberg going on a boat ride with his best friends Akiva Schaffer and T-Pain. This is easily one of the best rap songs written by the comedy trio, as they successfully rhymed “flippie-floppies” with “flipping copies.” Plus, it had the added bonus of Akiva and Andy constantly poking fun at Jorma for not being invited on their boat ride, AKA the standard for their exaggerated comedy stylings.

6. "Two Worlds Collide" f/ Reba McEntire

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Original Air: Nov. 21, 2009

This short was truly the archetype for not knowing what to expect from Samberg and his infuriatingly funny friends. “Two Worlds Collide” stars Samberg as himself and Kenan Thompson as a random guy who found a wig in a dumpster and convinced Samberg that he’s Reba McEntire. It plays on Samberg’s recurring role as an ignoramus with no sense of reality, and depicts him falling in love with Thompson and not listening to the criticisms of his friends trying to tell him that he’s not actually dating the real Reba. Thompson delivers a lot of memorable lyrics (“Ever since I came out my momma’s butt,” for example), but it’s impossible to unhear his battlecry of “I’m Reba!” over and over again. 

5. "Jack Sparrow"

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Original Air: May 7, 2011

After inviting Michael Bolton to sing on a track with them, The Lonely Island boys learn the hard way that he’s a movie fanatic who can’t shut up about Pirates of the Caribbean in this short from 2011. While the boys are trying to rap about their lavish lifestyle, Bolton is belting about Captain Jack Sparrow and his fearless adventures. It’s refreshing and hilarious to see the tables turned on Samberg, Taccone, and Schaffer, who would normally be the ones ruining a song with their niche interests, and their confused “what?”s and “nope”s in response to Bolton’s off-topic lyrics are textbook examples of flawless comedic timing.

4. "Motherlover"

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Original Air: May 9, 2009

If this song wasn’t about banging your best friends mom, it would honestly slap. “Motherlover” was the follow-up short to “Dick in a Box,” and reunited Samberg and Timberlake as those half-creepy/half-sexy R&B boys singing about sleeping with each other’s moms on Mother’s Day as a favor to one another. The song is twice as hypnotic as its predecessor, and the hook is about as clever as they come from the Lonely Island boys. It’s another incredibly accurate depiction of the sex ballads we love to sing along with, and immediately became a viral sensation.

3. "The Shooting AKA Dear Sister"

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Original Air: Apr. 14, 2007

Dear sister,

By the time you read this blurb, I’ll be dead...just kidding. But this short from 2007 did in fact make a killing when it was hyped up on the internet and recreated by many. “The Shooting AKA Dear Sister” is another musicless short that parodied an episode of The O.C. and depicted Samberg suddenly shooting Bill Hader as he wrote a letter to his sister before a string of shootings between Hader, Samberg, and a few other characters takes place. Repetition is one tool used in shorts that always seems to work, so playing the bridge of “Hide and Seek” by Imogen Heap every time a gunshot occurs was the perfect way to mock the teen drama. This short classically conditioned us to think of SNL every time we hear the phrase “Mmm whatcha say,”—sorry, Jason Derulo.

2. "Natalie’s Rap"

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Original Air: Mar. 3, 2006

One word to describe this short: BARS. Natalie Portman starred as an altered version of herself in her very own digital short when she hosted in 2006. In an interview with Chris Parnell, Portman responds to questions about her life in an explicit, hardcore rap, with claims that she’s essentially an uncontrollable monster. Portman confessing to smoking weed while she was a student at Harvard and slapping Seth Meyers across the face are just the tips of the iceberg in this short, which is similar to the “United Way” short in that it took a beloved celebrity and turned them into a reckless animal. Samberg appears at the end as a singing viking who supports Natalie’s wild tendencies, but Portman stole the show in this short that quickly became a fan favorite for turning America’s sweetheart into a stone-cold rapper. She and Samberg even returned for a sequel earlier this year with a more modern sound. No more questions.

1. "Lazy Sunday"

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Original Air: Dec. 17, 2005

Only the second ever digital short to air on SNL, “Lazy Sunday” was one of the first videos to go viral on YouTube when bootleg versions of it were uploaded overnight and accrued over two million views in a week. The video featured Samberg and fellow cast member Chris Parnell rapping about spending their Sunday morning going to Magnolia Bakery for cupcakes before catching a matinee of The Chronicles of Narnia. It’s mundane and low-quality, but it’s also regarded as one of the videos that sparked YouTube popularity and goes down in history as the video that kick-started a cultural reckoning with the introduction of digital shorts to SNL. Now pass that chronic—WHAT—cles of Narnia. 

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