What Are The All-Time Funniest SNL Sketches Starring Musicians?

Drake served as both the host and musical guest on Saturday Night Live last night, marking the 27th time in the show’s 38 seasons that an individual was asked by Lorne Michaels to pull double duty; if you’re keeping score at home, Lady Gaga also did double duty back in November. It’s been a minute since we’ve seen Drake act, but any traces of rustiness were not apparent when he stepped on stage in Studio 8H last night. More on his work momentarily, but first, we’re curious: What other musicians did the best job of being hilarious during sketches AND singing their faces off?


Before we get into the specifics, it’s important to know who we’re talking about here. Here’s a complete list of musicians who have pulled off the very difficult task of being both host and musical guest of the same episode of Saturday Night Live:

11/20/76 – Paul Simon
11/12/77 – Ray Charles
5/22/82 – Olivia Newton-John
5/7/83 – Stevie Wonder
2/21/87 – Willie Nelson
4/15/89 – Dolly Parton
1/19/91 – Sting
12/7/91 – Hammer
2/28/98 – Garth Brooks
5/13/00 – Britney Spears
2/10/01 – Jennifer Lopez
2/2/02 – Britney Spears
10/11/03 – Justin Timberlake
4/10/04 – Janet Jackson
10/9/04 – Queen Latifah
11/18/06 – Ludacris
12/16/06 – Justin Timberlake
11/7/09 – Taylor Swift
2/27/10 – Jennifer Lopez
4/2/11 – Elton John
5/19/12 – Mick Jagger
10/20/12 – Bruno Mars
2/9/13 – Justin Bieber
3/9/13 – Justin Timberlake
10/5/13 – Miley Cyrus
11/16/13 – Lady Gaga
1/18/14 – Drake

So, what were some of the most memorable sketches from these 25 years? Let’s review!

5. PAUL SIMON IS A TURKEY (Season 2 – 11/20/1976)
Paul Simon has been one of the most frequent guests on SNL over the years, making 18 total appearances on the show. He’s been a part of many memorable events in the show’s history—his stirring rendition of “The Boxer” in the episode that followed 9/11 still brings tears to our eyes—but his most iconic to this day still has to be the time he showed up wearing a turkey suit to do the monologue and sing “Crazy All These Years.” (We wish we could show you a clip, but SNL is notoriously protective of their material. You can see it on Netflix, though!)
http://www.youtube.com/watch?v=sAagUcfAYHY
4. JUSTIN BIEBER’S GOT GLICE (Season 38 – 2/9/13)
We wish we could say that The Biebs’ first (and likely last) time pulling double duty was successful but, in fact, it was exactly the opposite of that. Widespread rumors of Bieber’s diva behavior on-set circulated in the days immediately following his semi-disastrous appearance, all of which were confirmed by SNL legend Bill Hader during an interview with Howard Stern. Still, the Biebs is part of history with the sketch you’ll see above, one in which Taran Killam endlessly needles Bieber’s character for an awkward choice of words.

3. BRUNO MARS INTERNS AT PANDORA (Season 38 – 10/20/12)

When Bruno Mars was announced as both host AND musical guest on SNL, many initially scratched their heads. Of course, his talent as a musician is unquestioned, but who knew that he actually had comedy chops? Bruno solidified his future as a multi-hyphenate with this sketch where he appears as Devin, a Pandora intern who is called on to save the company from crisis with his impressions of Green Day, Aerosmith, Katy Perry and more.


2. BRITNEY’S DOO DOO PIE (Season 25 – 5/13/00)

Ah, remember the days before Britney got a lobotomy (allegedly)? She used to have so much pizzazz and verve! Even her biggest fans would agree that hasn’t been the same since the head-shaving incident of 2007, but this vintage clip of Britney’s first of two times where she played both host and musical guest shows her at the apex of her America’s Sweetheart stage. Here, she stars as herself alongside Tracy Morgan’s Woodrow, a sewer-dwelling homeless man who sings surprisingly tenderly about doo doo pies and firecracker beers.

1. JUSTIN TIMBERLAKE ANSWERS THE ETERNAL QUESTION, “WHAT’S IN THE BOX?” (Season 32 – 12/16/06)

You didn’t think we’d forget Justin Timberlake, did you? He’s the undisputed king of SNL Double Duty, having pulled off that feat more times than anyone else in history (3 so far, but he’ll almost certainly do more). And when you think of Timberlake and SNL, what do you think of? Dicks in boxes, natch.