The 5 Funniest Shows I Could (And Do) Watch Over and Over

Content Warning: Comedy is extremely subjective, and just because I enjoy a show does not mean you will feel the same way. Some of the shows I reference will contain humor that some people may find unpleasant or, at the very least, extremely dark. If a show on this list is not your cup of tea or you object to its content, that is your right. The last thing I want to do is suggest someone watch a program they find offensive, so please remember that these recommendations are based on my history and my tastes.

When life gets hard and crappy, I love to retreat into the world of sitcoms and weird, funny shows. I owe much of my sense of humor to the strange garbage I’ve watched on TV, from Adult Swim marathons I was far too young for to old reruns of “Three’s Company.” I am indebted to this strange garbage for lifting me out of funks and reminding me that although the world can seem overwhelming, we’re all in it together.

I don’t think there’s a way to talk about comedy without sounding like the most aggressively unfunny person in the world, so I will say that all of these shows have managed to hit on some truth in my life. Truths like feeling inadequate or your life isn’t going how you’d hoped. So I hope that if you watch any of the shows I’m about to recommend, you feel a little more seen. Or, at the very least, you find a new method for killing half an hour.

One: The Oblongs, streaming on Tubi

So grotesque and yet so sweet

“The Oblongs” was an odd little show from 2001 that only made thirteen episodes. Based on “Creepy Susie and 13 Other Tragic Tales for Troubled Children,” this show was about a strangely wholesome family who lived in the polluted Valley. Due to this literal toxic environment, all of the main characters who live in the Valley, including the members of the Oblong family, have severe congenital disabilities. 

Y’all, this is a dark show. But it’s also one of the funniest shows I’ve ever seen because the writing is sharp and packed with scathing social commentary. Of course, it helps that the patriarch of the family, Bob Oblong, is a 1950s stereotype voiced by Will Farrell. Bob Oblong is the best kind of boring man, the kind of person who shouts, “we’re eating soup! With garlic croutons!” as if that’s the most exciting thing to happen to him in years.

I would also like to clarify my feelings on using disability in the show. I believe it is up to viewers to draw their own boundaries on what they consider funny and appropriate. Regarding “The Oblongs,” I find I’m able to enjoy the show because I never feel as though the disabilities of the characters are the butt of the joke. It’s a dark comedy, but I feel the humor comes not from the disabled characters themselves but from the grotesque society they live in. The kids and the adults from the Valley live in poverty in a toxic wasteland, but their lives are happy. It’s dark, inspiring, and hilarious.

I’ve watched this show multiple times, and as much as I’ve appreciated the social commentary (which is usually just a form of “eat the rich”), it didn’t land until I saw the profoundly overrated dark musical comedy “Urinetown” (which also premiered in 2001). The episode “Flush, Flush, Sweet Helga” bares some remarkable similarities to the musical, as there is literally a scene where the rich people from the Hills take over the Oblongs’ bathroom. The rich folk barge into the Oblongs’ home, install a money-operated bathroom lock on the bathroom door and then charge $100 for each person who wants to go. I would have loved it if “Urinetown” had just been a musical version of this show.

Two: 30 Rock, streaming on Peacock

Is this an obvious suggestion? I hope it is because you may know how good this show is. “30 Rock” is about Liz Lemon, played by Tina Fey (also the creator of the show), the head writer of an SNL-type show called “TGS,” and the garbage insanity she has to deal with to put on a weekly show. In her corner, she has Jack Donaghy (played to perfection by Alec Baldwin), an NBC executive who decides to mentor her. Other incredible actors, like Jane Krakowski and Tracey Morgan, round out the impressive cast, though the show regularly boasted award-winning guest stars, like Matt Damon and Al Gore.  

The best description I’ve ever heard of this show is that it’s like a live-action cartoon. It’s the kind of show where a lion could be released in the studio, and we in the audience wouldn’t bat an eye because what else did you expect to happen when your show’s producer cuts corners and hires the world’s cheapest lion keeper?

I will always have a deep-abiding love for the episode “The Bubble” because it was the first episode I ever watched. Liz Lemon thinks her life is perfect because she’s dating a gorgeous doctor, played by Jon Hamm. Then she realizes this “doctor” is a dumb idiot but has been receiving preferential treatment his entire life because he’s so handsome. Liz tries to bring him out of the bubble into the real world, where people are mean and pretend to judge you based on merit, but he cannot stand the cruel, harsh world, so he retreats back into his glittering world of handouts and unearned praise.

“30 Rock” ended after about seven seasons, which is pretty impressive for a show that not nearly enough people watched. Fans of 30 Rock may feel better knowing the shows “Great News” and “The Unbreakable Kimmy Schmidt” have enough similarities to feel like you’re watching the same show.

Three: Man Seeking Woman, streaming on Hulu

Dating sucks.

Everyone knows it, and almost every person you meet will have a delightful horror story about a date gone wrong (except for the lucky bastards who married their high school sweethearts). However, “Man Seeking Woman” is a 2015 show that embraces the horrors of finding love and cranks those awful scenarios up to 11. Loosely based on the book “The Last Girlfriend on Earth” by Simon Rich, “Man Seeking Woman” follows Josh Greenberg, played by Jay Baruchel, as he’s dumped by his long-term girlfriend Maggie and forced to try to find love again.

Josh is unlucky in love, but he has his wise, older sister Liz (played by Britt Lower) and his douchey best friend Mike (played by Eric André), who is always by his side, ready to cheer him on.

I love how the show uses surrealist comedy to exaggerate real-life events, like how a date with an unattractive person becomes an evening of terror with a literal mountain troll. Or if you have trouble picking up women at a bar, it’s probably because you never met the wizard who visits all young men going through puberty and shows them how to hypnotize women. (Sorry about that, bro. I guess you just have to… talk to them or something?)

This is one of the few shows I recommend to people staunchly against fantasy and science fiction (like my sister, Bean, who refuses to watch anything “not real”). The exaggeration is so ridiculous but incredibly accurate that it’s impossible not to relate to the characters and their experiences. Sure, I’ve never traveled through time to try to heal things with an ex, but then again, haven’t a lot of us wanted to make something work with someone who just wasn’t right for us?

Four: Galavant, streaming on Hulu

Dan Fogelman knew he was lucky to get a second season of “Galavant,” and by God, he made a meal of it.

“Galavant” was an absolute musical gem. Starring Joshua Sasse as the titular character, “Galavant” was about a heroic knight who loses the love of his life, Madalena, to the evil King Richard, played by Timothy Omundson. Galavant sinks into a horrible depression and is only roused by Princess Isabella, who begs Galavant to defeat King Richard and rescue her people from his terrible clutches. Except, as we watch the show unfold, we realize that the evil King Richard is kind of a little bitch, and Madalena, played by Mallory Jansen, is the real brains behind the operation.

“Galavant” was a fantastic show that felt like if “Spamalot,” “The Neighbors,” (also by Dan Fogelman), and “The Princess Bride” had a baby. The show’s ridiculously catchy songs were written by Oscar-winner Alan Menken and his writing partner, Glenn Slater. Moreover, the music from that show managed to cross an impressive berth of musical genres, ranging from rock to operetta.

It’s also one of the few shows with a better second season, as it paired characters like Galavant and King Richard together as the world’s most unlikely duo (and best friendship, at least in King Richard’s eyes). Timothy Omundson is tragically pathetic as the wimpy King Richard. However, he plays the character so well that you’ll root for him even when he’s an antagonist (though he gradually transforms into a heroic character. WITH A DRAGON.)

If you love fantasy or adventure or just the works of Alan Menken, then you’re going to love “Galavant.”

Five: People of Earth, streaming on Hulu

I am devastated this show was renewed for a third season (which was written and ready for production!) only to be canceled at the last minute. The first two seasons of “People of Earth” are funny, clever, and heartwarming. Wyatt Cenac stars as Ozzie Graham, a New York City journalist, as he travels to rural New York to interview a support group called “StarCrossed.” All of the members of StarCrossed are individuals who have survived alien encounters and abductions. Ozzie thinks everyone in the group is crazy until he begins to dig into his past and realizes that he has had his own alien encounters.

People of Earth boasts a superb ensemble, including SNL alum Ana Gasteyer as the support group’s leader and other talented people like Luka Jones, Brian Huskey, Alice Wetterlund, and Da’Vine Joy Randolph. All the characters are charming, interesting people, though my absolute favorite was Don the White, played brilliantly by Björn Gustafsson. Don the White is a good guy who technically works for the bad guys, but man, does he have a pure heart. This sweet alien bumbles his way through social interactions and his various jobs and still manages to steal the heart of Kelly, the part-time temp. (There’s a reason I want to fancast him as Dagesh in the Ice Planet Barbarians TV Show)

Please enjoy watching this quirky show, and then get angry with me when you learn there’s no season 3. Then, maybe we can collectively demand David Jenkins release the scripts? Assuming he’s not too busy with “Our Flag Means Death.”

Are these the only funny shows I’ve ever watched? Absolutely not, but they are all finished and ready for you to binge the next time you feel like avoiding the outside world. If I were you, I’d start with “People of Earth,” because it makes you hope that the next weirdly tall Nordic cutie you interact with may be the alien man of your dreams.

3 thoughts on “The 5 Funniest Shows I Could (And Do) Watch Over and Over

  1. I cannot believe someone else loves The Oblongs! I love that show! I wish it had continued past 1 danged season. I never really saw them as disabled, I guess. I always thought of them as mutants….victims of the toxic place they live below the rich folks. It was definitely a commentary on the destruction of our environment brought on by our constant polluting of our environment; and how the poor will ultimately pay the price far more than the rich.

    I also loved Galavant, and wish that it too lasted longer! I may have to rewatch!

    I will check out the other shows you list. I have, of course, seen 30 Rock. Have you tried watching Pushing Daisies and Eli Stone? Unfortunate victims of a writers strike, and sadly not many seasons. What seasons there are are definitely worth checking out.

    My go-to for re-watching over and over again is Archer! So smartly written, excellent voice talent, lots of easter eggs if that is your thing…..like things on the mad scientists screen that lead you a merry hunt on the interwebs.

    My go-to movie is The Princess Bride. I also love A Knight’s Tale, Nightmare Before Christmas, Young Frankenstein, to name a few….

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    1. Mary, I love your suggestions! I’ve heard of Pushing Daisies, and everyone I know who watched it was absolutely in love. I haven’t heard of Eli Stone, but I’ll look it up! Thank you for telling me about these great shows! It’s sad how the writer’s strike (who I will always be very much on the side of) led to the end of so many good shows. I think “Terminator: The Sarah Connor Chronicles” was one of those shows that suffered because of it.

      And I love that we have so many tv shows in common! Archer is one of my absolute favorites, and I think H Jon Benjamin has a fantastic voice. It’s wild how he plays such different characters in “Archer” and “Bob’s Burgers.”

      Also, 1000% agree with you on how sad it is that “The Oblongs” was cancelled. I think it made a few salient points about social division and the negative impact that the wealthy have on the environment (which considering the current conversation over ridiculous celebrity private plane flights, is very very much STILL worth discussing).

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