100 Funniest Sketches Of All Time (40 – 31)

The funniest sketches of all time continues. Today’s selection is a mix of mad music, surreal monologues and unexpected twists. Here are sketches 40 through 31

In case you missed it: 

40. Business Time – Flight of the Conchords

The Flight of the Conchords are just so good. They never fail to make me laugh. I remember watching the show on HBO and loving their sense of humour. It was also one of those rare times where I was impressed by the musical comedy numbers. So often they can fall flat or be a bit one note (forgive the musical pun) but with them where was musical craft and real thought in the comic writing of the lyrics. This song is probably their most well known (the live version is even better I reckon) and for good reason, it is a fantastic mix of madness, melody and comic timing. The chorus will now be stuck in your head for days. You’re welcome. 

39. Mr. Robot - Eugene Mirman

Years ago at a comedy gig in New York this bedraggled comedian called Eugene Mirman got up onstage and took off on the most odd flights of fancy in his routine. Half the audience was bemused. I was laughing my head off. His offbeat sense of humour really connected with me. To say it was surreal would do it a disservice. It was just quirky and unlike other stand up I had ever seen. He made choices that were fresh and unusual to my ears. I immediately picked up his album and I never looked back. It’s fair to say I am a huge fan. This kooky sketch is a great example of his unique brand of comedy. It is pure fire. But it begs the question “Is fire an emotion?”

38. Language - A Bit of Fry & Laurie

Many moons ago, a friend of mine loaned me a VHS tape (yes, I’m that old) of several episodes of “A Bit of Fry & Laurie” and it was like discovering a comedy goldmine. The sketches were smart and clever, with a very particular sensibility that spoke to me. This was a type of sketch comedy I hadn’t really seen before. They trusted their audience’s intelligence and they were happy to tackle highbrow topics. And just as readily they could throw in simple silly one liners. It was my kind of show and I still love it. I had to return the VHS tape long ago but I have since found many of my favourite sketches online, including this one. 

37. Taxi Driver Confessions - Chris Rock Show

One of the most fun experiences I had while living in New York was attending a taping of The Chris Rock Show. It was on HBO and usually featured an interview, some sketches and a musical act. On the night I was there he interviewed Cedric The Entertainer and the musical act was Nas (who was so high he had to start his song again). Grandmaster Flash was perched up in a booth above the audience and was spinning amazing tunes in the downtime between recording set-ups. The sketches that night were a bit hit and miss, but the piece that stood out was his funny take on a popular HBO undercover camera show at the time called Taxicab Confessions. Chris Rock went out in a New York yellow cab and actually picked up real passengers, and they recorded the conversations and broadcast them on his show. Nothing is funnier than real interactions with New Yorkers. And hats off to Chris Rock for his on-the-spot thinking and conversational skills. Watch and try not to laugh. 

36. The Sopranos - Mad TV

Mad TV wasn’t ever really on my radar but I had heard it mentioned so many times on podcasts  in the intervening years, I knew I had to find some of the best sketches and watch them. This one, which must have come out at the height of The Sopranos fervour, just made me roar with laughter. The idea of putting a show like that on the heavily censored, sterile world of American network television was a comedy gift waiting to happen. There’s lots to love about the near-perfect performances in this sketch, but the real star of the sketch is the video editor. He deserves a big pile of gabagool.

35. People Buying a House - Mitchell & Webb

If you’ve ever watched daytime TV in Britain you will definitely have seen this show parodied so expertly by Mitchell & Webb. Much like the previous sketch, the jumpcuts are the unsung hero here. A simple sketch but like so many of theirs, they absolutely nail it. Just like Jeff’s shelves.

34. Four Candles - The Two Ronnies

The Two Ronnies are masters of playing with words and this sketch might just be their finest example of that. Lets light a candle for their contribution to comedy history. In fact, lets light four candles. 

33. Boyfriend - Snuff Box

Matt Berry is almost always the same in everything he does, but that’s absolutely fine with me, because Matt Berry being Matt Berry is always hilarious. Before seeing this set of sketches I knew him from The IT Crowd and Garth Marenghi’s Darkplace, and have since loved him in Toast and What We Do In The Shadows. There is something magnetic about him. When I first discovered this recurring sketch from Snuff Box I dont think I’ve ever laughed so hard in my life. The premise is so simple (ridiculous and predictable even) but it is 100% hysterical thanks to Matt Berry’s delivery. I don’t know how many times I have seen these, and despite knowing the punchline a mile away, it always gets me. If you dont like it, then F*#k You!

32. Fish Slapping Dance - Monty Python

This little underrated gem from Monty Python is as good as anything they made. Short and sweet. Unlike the fish.  

31. Del Boy - Stewart Lee's Comedy Vehicle

Stewart Lee is an absolute hero of mine. I was a huge fan of Fist of Fun back in the day, and even more so his series Stewart Lee’s Comedy Vehicle. This sketch is that series crowning achievement. After a lengthy rant about the British public’s choice of their favourite funny moment (Del Boy from Only Fools & Horses falling through the bar), the show cuts to this ludicrous sketch about Del Day, which manages to elevate the whole thing to a level of high comedy art. I love his commitment to the madness of the central idea of celebrating the day people first witnessed Del falling through the bar, and I imagine he spent the bulk of his series budget on just this sketch alone. Money well spent. It is a thing of genius. 

The sketch countdown continues…



100 Funniest Sketches Of All Time (50 – 41)

Past the halfway point in the list of 100 funniest sketches of all time. Today’s batch of ten sketches are all pure gold. Here we go then from 50 – 41

In case you missed it: 

50. Brilliant – The Fast Show

The Fast Show was BRILLIANT. Paul Whitehouse might be one of my favourite comic actors and this silly recurring sketch is a brilliant showcase of his abilities. I always loved the way they pieced these particular sketches together with multiple takes and then stitched them into something almost arty. In a strange way, the rapid fire style of The Fast Show was a real precursor to the shortform content we see everywhere on TikTok and Reels now.

49. Mastermind - The Two Ronnies

The Two Ronnies at their clever, crackling best. This sketch is a great example of what I loved the most about them. It starts with really sharp writing. They have crafted it and shaped it on the page, and I love to imagine them seated together going over every line, perfecting it, tightening up the jokes, sharpening the segues. And then when it comes time to perform it, (which they do really well) it all flows so effortlessly because they put the time in to write it so thoughtfully. For me, this sketch is a hall of fame contender for writing.

48. Jazz Club - The Fast Show

Jazz Club on The Fast Show was the same joke every time, but what a joke. It was GREAT. For me personally it resonated even further. My dad was a big fan of jazz and it was consistently the sound that bounced out of the speakers in our house. It is part of my creative influences almost by osmosis. So, this sketch, while making fun of the pretentiousness of jazz fans and certain musicians, I still see deep affection for jazz in there. 

47. Argument - Monty Python's Flying Circus

I’d like to have an argument please! Probably my favourite Monty Python sketch. So simple and so well done. Michael Palin at his mild mannered best and Cleese & Chapman are snarkingly perfect. For the longest time Cleese was my favourite Python probably because of his physicality and my deep love for Fawlty Towers, but as I get older I relate more and more to the amiable Palin who has a kind of innocence and confusion about him that feels very real. In lesser hands this sketch could easily gone nowhere, but Palin keeps it anchored in something human and that is why I love it so much. 

46. Cake - BrassEye

There are precious few people who deserve the title of genius to be bandied about with their name. But for me, Chris Morris is most certainly in the conversation. BrassEye was Chris Morris at his scathing, sharp best. Building on his cleverly crafted The Day Today, he really pushed his satire of the bombastic television news industry to a new level with this show. I will never forget the first time I saw the Cake segment on the show. It was the first time I can remember seeing a show blur the lines between reality and fiction, and I was amazed at his ability to dupe unsuspecting celebrities and politicians into talking on camera about “a made up drug” and then to cut it together into this preposterous news report – which makes it equal parts jawdropping and hilarious. Sacha Baron Cohen went on to make this type of stuff his trademark, but Chris Morris is one of the master craftsmen who built those foundations with BrassEye. A show that has never been equalled and it had a huge impact on me.

45. Social Class - The Frost Report

This was one that I came across when I was down a deep nerdy sketch comedy rabbit hole on YouTube one night. This is like seeing a supergroup of comedy – John Cleese, Ronnie Barker and Ronnie Corbett – in a sketch written by Marty Feldman (my favourite person in the brilliant Young Frankenstein movie). Visual and verbal comedy at its finest -Sight gags mixed with social satire. I look up to this kind of thing.

44. Soupy Norman - Barry Murphy & Mark Doherty

Soupy Norman by Barry Murphy and Mark Doherty was a thing of genius. They took a Polish soap opera called “First Love” and re-dubbed it with Irish comedians into a coming of age story of a Cork girl moving to Dublin. The choice to make the dialogue a ‘Bad Lip Reading’ style delivery, rather than make any true sense only adds to the silliness and fun of it. Probably the funniest thing to have ever been produced by Irish TV and you can thankfully find all 8 of the episodes on YouTube. It’s definitely one of the things I share the most with others when they ask me about the funniest thing I have seen. True brilliance at work.

43. Borat - Sacha Baron Cohen

Before his global renown, Sacha Baron Cohen had a golden period as the most interesting and edgy comedian around. It was amazing to watch him go out into the world and take real chances with his comedy characters in very real (and sometimes dangerous) situations. His Kazakhstani journalist Borat has worn out his welcome a bit by now, but there was a time when this magnificently awkward, idiotic character was as fresh as anything I had seen. This song is probably my favourite Borat moment. It is him at his best, using comedy to prod society and expose their ignorance, while holding an uncomfortable mirror up to their blinkered beliefs, and still be really really funny.

42. I Said Bitch - Key & Peele

Key & Peele are just excellent at what they do. This sketch is an undeniable little masterpiece. Starting with a super simple idea, they build on it slowly and continue to escalate it to such ridiculous extremes. And it feels properly cinematic in its execution. I think about the time and money it must have cost to put this one sketch together, but they had such belief in the idea and knew it would deliver a bigger impact if they went all in. I love that about it. 

41. Heroin Galore - The Fast Show

The Fast Show was consistently hilarious and sometimes their one-off sketches were funnier than their recurring characters simply because they seemed fresh and unusual. For me, they were often at their best when they did these stylish, note-perfect parodies of BBC programming. I learned after seeing it that it was a take on the famous film Whiskey Galore albeit with a very different cargo. The decision to make it in black & white also really stands out and is the kind of attention to detail I love. 

The sketch countdown continues tomorrow…

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 


farewell terry jones – monty python master

Monty Python were my comedic heroes as a teen. They opened a window into a world of the absurd and weren’t afraid to take bonkers chances and make unusual choices. And boy did they make me laugh. I remember poring over the scripts as much as watching the sketches themselves. Master craftsmen. And Terry Jones was such a cornerstone of that madcap genius they made for the world. May he rest in peace – “He’s not the Messiah, he’s a very naughty boy”