Ranking 15 of the Best ‘SNL’ Digital Shorts

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This past weekend, Jorma Taccone, Justin Bieber and Andy Samberg were amongst those celebrating Saturday Night Live’s 100th digital short in a new video featuring nods to the show’s best-of skits. The Lonely Island crew taught Bieber how to celebrate the occasion — and it’s as lewd as you’re thinking — while celebs like Natalie Portman made cameos, reprising their famous Digital Shorts’ characters. Never one to miss a celebration — particularly when it comes to one of the most reliable laughs on the long-running comedy series — we wanted to rank a few of the best SNL Digital Shorts of all-time. It was a supremely difficult task, but we left you plenty of room to drop your faves in the comments section. Head past the break — where we chat about male genitalia far more than you did today — to take a look (including brand new #100).

Digital Short #100

1. Natalie Raps

Just two years after her manic pixie dream girl role in Garden State, Natalie Portman cinched the crush everyone already had on her with a foul-mouthed rap poking fun at her pristine public image. The actress tapped into her inner Black Swan and became a true “badass bitch.” What you want, Natalie?

2. Jack Sparrow

Michael Bolton’s “sexy hook” for the Lonely Island guys becomes increasingly Jack Sparrow/Johnny Depp obsessed and weird (yes, just like Tim Burton). Plus, there’s Michael Bolton in drag and Michael Bolton singing about mountains of cocaine.

3. Dick in a Box

The smooth 1990’s R&B sounds of Justin Timberlake and Andy Samberg helped make SNL’s Digital Shorts a pop culture phenomenon with this ditty about a very special holiday gift. The short was created to showcase Timberlake’s singing abilities, and after it became a viral hit, the star was a regular player with The Lonely Island. The song also won a 2007 Creative Arts Emmy Award for Outstanding Original Music and Lyrics and prompted the sequel, Motherlover.

4. Motherlover

A testament to how cool Patricia Clarkson and Susan Sarandon are for being the object of lusty Lonely Island affection. Motherlover is the second best idea Timberlake and Samberg have ever had, according to them.

5. Jizz in My Pants

Pure electro-trash douche chill.

6. I’m on a Boat

The ultimate rap video cliché that went platinum in the US, won a Grammy nod, and spawned a boatload of YouTube imitators.

7. Iran So Far

Andy Samberg’s love letter to Iranian President Mahmoud Ahmadinejad with the perfect Aphex Twin sample, Jake Gyllenhaal, and Maroon 5’s Adam Levine’s signature falsetto.

8. Lazy Sunday

2005’s mundane-inspired rap Lazy Sunday won the Digital Short series a regular spot in the SNL lineup after becoming an overnight viral hit, injecting some much needed life into the show.

9. The Curse

Jon Hamm becomes The Lost Boys’ sweaty sax player Tim Cappallo in this horror lovers’ parody, which also spoofs Sam Raimi’s Drag Me to Hell — complete with gross-out ending.

10. Shy Ronnie

Rihanna and Andy Samberg’s partly inaudible duet won an Emmy nomination and proved the singer had decent comedic chops.

11. Laser Cats!

All we need in this life of sin is Bill Hader shooting cats that pew pew lasers out of their mouths. The 2006 short is a low-budget fever dream, shot around the SNL offices.

12. Body Fuzion

This funny ladies only aerobic workout combinines public access television weirdness with 1980’s VHS nostalgia — a fuzion of big hair and lycra.

13. The Japanese Office

Still funnier than most of the new season of The Office.

14. V-Necks

Ben Stiller puts American Apparel to shame and proves he’s the right guy to pull off a deep v-neck tee… until he gets arrested.

15. Sloths

Before the Honey Badger became an internet celebrity, Sloths were a thing thanks to Staten Island Tech High School’s pervy documentary anthem featuring the three-toed creatures.