100 Funniest Sketches of All Time (60 – 51)

My carefully curated list of the 100 funniest sketches of all time continues. Today’s selection is a mix of classics and lesser known gems. Here we go from 60 to 51.

In case you missed it: 

60. Put a Bird On It – Portlandia

Portlandia had a cult following for its run. I was a fan of Fred Armisen’s comedy and I adore Carrie Brownstein’s band Sleater Kinney, so I had high hopes for it, but I never totally connected with the show. For some reason I felt it was trying a little bit too hard or something. That said, this sketch was one that stuck out. In particular I love the moment in the sketch when an actual bird arrives on the scene. The lesson here is clearly, if in doubt, put a bird on it. 

59. The Valets Love Liam Neesons - Key & Peele

A list of sketches like this could almost include all of Key & Peele’s sketches. They are that good. My favourite recurring characters were the valets and the enthusiastic nutty conversations they had. A lot of it is in the ridiculous over-the-top energy of it, but also the decision to always have a crazy ending to close them out. Ending a sketch is such a tricky thing sometimes and they always decided to go big, which felt right, especially because it became something I would eagerly anticipate every time one of the valet sketches appeared on the show. This particular sketch has now entered the lexicon in my household, to the point where we refer to the actors solely now as Liam Neesons and Bruce Willy. 

58. Last F**kable Day - Inside Amy Schumer

I never got a chance to watch Inside Amy Schumer when it was on, but I was sold as soon as I was sent a link to this star-studded sketch featuring entertainment icons Tina Fey, Julia Louis-Dreyfus and Patricia Arquette. I loved her clever take on the unreasonable demands on women in the entertainment industry, while also sticking the landing on a seriously funny sketch. 

57. History of Punk - Saturday Night Live

Fred Armisen appears on this list once again, this time with one of his Saturday Night Live sketches that parodies punk era Britain brilliantly (with a lovely twist). Armisen’s affinity for the punk scene just beams out from the screen. You can’t help but smile seeing him and Bill Hader having bucketloads of fun. It’s not surprising that the two of them went on to expand this documentary-style sketch into short film length parodies on the superb Documentary Now series.  If you haven’t seen Documentary Now, you are missing out on a comedy masterclass down to every detail. 

56. Focus Group - I Think You Should Leave

I Think You Should Leave with Tim Robinson is a uniquely bonkers brand of sketch comedy. Not for everyone, but I absolutely love it. There’s a surreal vibe to a lot of them, but often done very subtly. One of the things that I particularly like is the unpredictability of the sketches and this one is a lovely example. 

55. Daves I Know - Kids In The Hall

Growing up in Ireland I wasn’t exposed to the Canadian cult favourites Kids In The Hall, so I came to their stuff later when I lived in America. But in a pre-YouTube world their stuff was hard to find, so I eventually got to catch up via d’internet. Like most sketch shows it was a bit hit and miss, but they were never better than this ridiculous song. If your name is Dave, you’re really gonna love it.

54. Dead Parrot - Monty Python's Flying Circus

This sketch is usually number one on most lists but this list is not in order of funniness, so I have popped it in here at the midway point to savour. It’s probably true to say that without Monty Python’s Flying Circus there really wouldn’t be a lot of the other sketches on this list. They were bright, brilliant, bonkers skits that influenced generations of comedy writers 7 performers, myself included. There is nothing I can say about this sketch that hasn’t already been said, other than the fact that it will likely leave you pining for the fjords. 

53. D**k In A Box - Saturday Night Live

Andy Samberg is a funny man (My son adores the sitcom Brooklyn 99 and we recently bonded over the ridiculous movie Hot Rod). Justin Timberlake also clearly has a sense of humour. Together they created the most foul-mouthed, Christmassy boyband ballad of all time. Juvenile humour never sounded as good.  

52. Nick The Lounge Singer - Saturday Night Live

I love the loose, freewheeling energy to this sketch. It feels like these early days of Saturday Night Live were a little less tightly scripted and they sometimes just set up a premise and let funny people do funny things. In fairness, a sketch with a young Bill Murray as a lounge singer at a ski lodge is a great set up (doesnt hurt to throw in Gilda Radner, John Belushi, Dan Aykroyd, along with Paul Shaeffer on piano). It meanders a bit but Bill Murray is committed to the bit and he has that inimitable glint in his eye that I’ve always loved. 

51. Spoonie Luv's Personal Ad - Crank Yankers

Crank Yankers was the brainchild of Jimmy Kimmel & Adam Carolla and featured some brilliant comedians doing prank phone calls. Those calls where then reenacted onscreen using puppets, which made them really unique in look and feel. Tracy Morgan’s calls (as the character Spoonie Luv) were always my favourite because they veered into his particular brand of madness, and the reactions from the other end of the phone were priceless. 

The sketch countdown continues… 

100 Funniest Sketches of All Time #50 – #41 


Chalkboard Quote #1 – Tina Fey on being creatively brave

I have an old chalkboard that I recently hung on the door to my office. I thought it might be interesting to occasionally write quotes that connect with me on the chalkboard. Subtle prompts and boosts to my creative confidence every time I enter the room. Then I thought it might be fun to share them here with you too. So, here is the first in a sporadic series of the chalkboard quotes upon my door. I started with a quote from Tina Fey because she is a writer and performer I utterly adore. It is a great reminder that you sometimes have to take a leap of faith creatively. Tina clearly did, and she seems to be doing great so far.