Best Web Series: And Their Funniest Characters

Best Web Series: And Their Funniest Characters

Continuing the theme of giving you the best web series that the internet has to offer, this time I thought we’d explore some of the funniest web native characters that I’ve seen.

Obviously, a list of the funniest characters can never be contained to just one page on a blog, so I did have to introduce some artificial parameters in making this list. First, the characters have to be a part of an episodic web series. I can’t possibly keep up with every short-form video put on the web, so trying to nail down the best characters who only showed their faces one time on a Vimeo player is impossible. Second, the characters have to be essential to the plot. Again, a character that comes in and just does his or her thing for 14 seconds of magic can be funny, but it takes true comedic excellence to keep me laughing for an entire episode or an entire season. And third, the character has to be relatable. Thus, in our list of the funniest characters from the best web series on the internet, I’ll be sure to let you know what makes the character both funny and relatable.

And if you don’t care to read the list, just take a look at the playlist I put together for your consumption, or check out the player at the end of the post!

Note: This post is full of spoiler alerts…so you’ve been warned!

Nicky – “The Pursuit of Sexiness“; UCB Comedy
Nicky, played by Nicole Byer, is absolutely one of the funniest characters I’ve seen in a web series. Right from episode 1, you can tell that both the series and Nicole are going to be a hit–right from the moment of silence she drops on her friend when the idea of paying for sex is raised during an absolutely inane phone call. The episode ends with the unfortunate substitution of an in-home movie for drunken sex, setting up a season of comedy gold for Nicole and her character. How is she relatable? Nicole keeps the party going, and who doesn’t love a friend like that? Does she sometimes go overboard, leaving you to pick up the pieces of her ill-fated attempt at fun, drama or sex? Sure. But admit it. Your life wouldn’t be half as interesting without her.

Thomas Wellington – “High Maintenance” 
Even if you’re a superfan of “High Maintenance,” you probably don’t recall the name Thomas Wellington. After all, the series is an anthology, so for the most part, characters don’t carry over into other episodes, and “Thomas” doesn’t happen to be the name of any of the episodes, which is “High Maintenance’s” way of telling us who the episode is about. Instead, Thomas Wellington, played by Theo Stockman, is a crazy into himself personal chef that is probably getting paid for jobs out of his league as he foolishly prepares bacon-wrapped matzah ball soup for a traditional Passover Seder. The episode ends with Tom getting jerked off by a vengeful daughter just as his weedman arrives at the front door of the unsuspecting mid-Seder-having family. How is he relatable? Everyone has that friend who thinks he’s a lot better at his job than he actually is, leaving you to wait until his overconfidence completely blows up in his face, thereupon allowing you to laugh at him, only to yield the last laugh to that same friend as he surfs on your coach 2 out of every 3 nights while looking for a new gig.

CeCe – “Awkward Black Girl“; Issa Rae
CeCe, played by Sujata Day, may not be the favorite in a tournament to win funniest character on “Awkward Black Girl,” but she’s my sleeper pick in any bracket! She constantly delivers pick-me up energy to an already energetic show, making it hard to ever get bored, especially when she’s on one of her “misadventures” down the road of misappropriating black culture to her black friend on the show. One of her funniest moments comes in a scene in which she helps that same friend record 16 bars in a studio. Her efforts are fairly ridiculous, but right in line with her character’s overall lack of self-awareness. How is she relatable? Not to sound too politically incorrect, but I think we all know someone who feels that they identify the most with a culture that’s genetically foreign to them. Not everyone takes it’s to the Rachel Dolezal level, but much like CeCe, their desire to belong to a non-native culture often yields both respect and hilarity.

Olivia – “Ackee & Saltfish“; Cecele Emeke
Olivia, played by Michelle Tiwo, is one of two main characters in the series, and while I mean no disrespect to her co-star Vanessa Babirye, she tends to steal the show. I first came upon this awesome series during this past year’s Tribeca Film Festival, and in speaking for all of New York City, one would have to say that this was one of the best web series to appear in the new Tribeca Now series. This web series, and Michelle Tiwo, are so good that I don’t want to spoil any of the episodes, especially Episode 1 about the potential of forgetting to buy Lauryn Hill tickets. But in talking about our funny character, Olivia tends to be the high-strung one with plenty of quick jabs and tid-bits that are dry in nature, but 100% smart-funny (if that’s a thing). How is she relatable? You know that friend that can go off on a tangent for 24 hours straight, completely forgetting anything and anyone that should be of priority to her during that timespan? That’s Olivia, and it’s that very tangential nature that allows her to be so funny, because for an entire webisode, she makes you suspend all disbelief in a way that not all web series or web series characters are able to do with the lack of exposition that often takes place as a result of the shorter format.

Mike – “That Guy“; Black&Sexy TV
Mike, played by William Catlett, may not be initially thought of as the funniest guy on the show I call the funniest web series on the internet, but when you get down to it, he’s hard to beat. Take this episode of “That Guy,” in which Mike goes through the struggles of trying to figure out whether he should “pop-up” at his girlfriend’s crib in order to see if she’s cheating on him. The entire scene is pure Mike, as he goes from being nervous, to insecure, to overconfident, and then to feeling stupid all within about 7 minutes of game tape. The rest of the series is much of the same, as Mike, a broke, insecure, bus-riding, wannabe-lothario, finds it hard being the best friend of a guy who is a little smoother with the ladies and “tends” to have his money right. How is he relatable? We all have a broke friend, right? And if you don’t know who it is…it’s probably you.

All that said, I’m sure there are many web series characters that I’ve missed. Feel free to let us know some of your favorite characters in the comments section below. And don’t forget to subscribe to our Newsletter or our YouTube channel!

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