SNL50 - Top 15 Digital Shorts

 

My parents wouldn’t like the content of this list. The Lonely Island consisting of Andy Samberg, Akiva Schaffer and Jorma Taccone go out of their way to push the boundaries in sexual content and just plain silliness. While the show benefitted from their awkward low budget filmed shorts, their songs were often the standouts. Since there are sequels to some of these, watching them in order may be confusing. I recommend watching 9 before 11 and watch 8 then 1 then 13. I’ve enjoyed listening to their recent podcast where they go behind the scenes of making each of these masterpieces. Here you go Quaid Army. Righteous Kill. Enjoy.

15. I’M ON A BOAT
EPISODE: S34E15 (02.07.2009)
HOST: Bradley Cooper
MUSICAL GUEST: TV on the Radio
This is the anthem for anyone getting on a boat for the first time. They are so excited! I feel a little bad for Jorma as T-Pain took his spot.
LINK: Click here (uncensored)

14. THE TIZZLE WIZZLE SHOW
EPISODE: S35E10 (12.19.2009)
HOST: James Franco
MUSICAL GUEST: Muse
This one gets dark pretty fast.
LINK: Click here

13. 3-WAY (THE GOLDEN RULE)
EPISODE: S36E22 (05.21.2011)
HOST: Justin Timberlake
MUSICAL GUEST: Lady Gaga
The conclusion to the Dick in a Box guys’ trilogy. Another catchy tune with awesome 90’s style.
LINK: Click here

12. JIZZ IN MY PANTS
EPISODE: S34E15 (12.06.2008)
HOST: John Malkovich
MUSICAL GUEST: T.I.
Can’t believe they got away with this on the show. Lots of facial expressions in this one. Love the quick edits in the middle. Also a quick JT cameo.
LINK: Click here (uncensored)

11. LAZY SUNDAY 2
EPISODE: S37E22 (05.19.2012)
HOST: Mick Jagger
MUSICAL GUEST: Mick Jagger
After they got to 100 Digital Short, their 101 went back to the original for a fun sequel complete with the return of Chris Parnell. Over the top fun!
LINK: Click here

10. HERE I GO
EPISODE: S50E07 (11.16.2024)
HOST: Charli XCX
MUSICAL GUEST: Charli XCX
As a 50^th anniversary treat, The Lonely Island made a couple Digital Shorts that showed they still have the magic touch. This song is so incredibly catchy, catty and fun. I don’t know why but I love when they sing “Have fun in central booking”.
AMERICAN LINK: Click here
CANADIAN LINK: Click here (uncensored)

9. LAZY SUNDAY
EPISODE: S31E13 (12.17.2005)
HOST: Jack Black
MUSICAL GUEST: Neil Young
While not their first Digital Short, this is the one that brought SNL into a new realm. With the start of YouTube at the same time, this is the short that everyone was talking about and started a new way of watching SNL for a new generation.
LINK: Click here

8. A SPECIAL BOX
EPISODE: S32E09 (12.16.2006)
HOST: Justin Timberlake
MUSICAL GUEST: Justin Timberlake
Justin Timberlake upped the song production value with this now Christmas classic. Where do they get these ideas?
LINK: Click here

7. I JUST HAD SEX
EPISODE: S36E10 (12.18.2010)
HOST: Jeff Bridges
MUSICAL GUESTS: Eminem, Lil Wayne
They are so happy. I like the crowds being interested in their accomplishment.
LINK: Click here

6. JACK SPARROW
EPISODE: S36E20 (05.07.2011)
HOST: Tina Fey
MUSICAL GUEST: Ellie Goulding
I like the mix of hard core and Michael Bolton’s utter silliness. Love that he did this.
LINK: Click here

5. GREAT DAY
EPISODE: S35E22 (05.15.2010)
HOST: Alec Baldwin
MUSICAL GUEST: Tom Petty and the Heartbreakers
Love the unhinged lyrics of this song. So fun.
LINK: Click here

4. DEAR SISTER
EPISODE: S32E17 (04.14.2007)
HOST: Shia LaBeouf
MUSICAL GUEST: Avril Lavigne
The only non-singing one on this list. But perfect use of Imogen Heap. Twenty times funnier if you’ve seen the second season finale of The OC which aired many years before this short. They must have enjoyed making dead faces.
LINK: Click here

3. NATALIE’S RAP
EPISODE: S31E13 (03.04.2006)
HOST: Natalie Portman
MUSICAL GUEST: Fallout Boy
Natalie Portman going this hardcore is hilarious. She proposed it to The Lonely Island who jumped at the chance to highlight her rap skills.
LINK: Click here

HONORABLE MENTION: NATALIE RAP 2
EPISODE: S43E13 (02.03.2018)
HOST: Natalie Portman
MUSICAL GUEST: Dua Lipa
Not technically a Digital Short as it is not made by Lonely Island. It’s a fun sequel and good on Andy for popping in for a cameo.
LINK: Click here

2. YOLO
EPISODE: S38E12 (01.26.2013)
HOST: Adam Levine
MUSICAL GUEST: Kendrick Lamar
Such a catchy song and some great advice for those who worry a lot. Love the visuals of this one.
LINK: Click here

1. MOTHER LOVER
EPISODE: S34E21 (05.09.2009)
HOST: Justin Timberlake
MUSICAL GUEST: Ciara
No one thought they could top the first one of this duo. They prove everyone wrong with an even more outrageous idea than a Christmas gift.
LINK: Click here