Samantha Bee And Mindy Kaling’s Hilariously Weirdo Pre-Fame Projects

How two of television's funniest people both got their start doing fanfic theater productions
Samantha Bee And Mindy Kaling’s Hilariously Weirdo Pre-Fame Projects

Here at Cracked, we are endlessly entertained by the “before they were famous” chronicles of our favorite artists. All of our entertainment heroes have fascinating origin stories – for instance, did you know that Nicholas Cage’s first movie role was in Fast Times at Ridgemont High?

Our latest favorite pre-fame projects are from Mindy Kaling and Samantha Bee, who each starred in bizarro pseudo fan fiction theater productions before hitting it big on The Office and The Daily Show respectively. Let’s take a look back at Samantha Bee’s shot at “Sailor Moon” and Mindy Kaling’s time as Ben Affleck in two amazing, outlandish, and completely unlicensed fan plays.

TBS Productions

I swear I'm not being gross - imagine her in a ‘Sailor Moon’ skirt

Before she would spend a massive 11 years on The Daily Show and long before she would host her own late night news satire show, Samantha Bee spent the bulk of her twenties in the exact same position as so many other young Canadians with dreams of seeing their faces on screens across the continent – she was waiting tables and auditioning for children’s theater productions in Toronto.

Said Bee about this time in her life, “I tried to be an actor in Toronto, and I did not get hired for two years. I waitered, I auditioned for things, but I did not get hired for anything, ever.” Of course, “anything, ever” would turn into “something” “eventually”, since we don’t typically write about artists who never once get work. 

When Samantha Bee was 26 years old, she was finally casted in a regional theater production. She even landed the starring role! Her first big break was as the titular protagonist in a touring children’s theater adaptation of the popular manga and anime series Sailor Moon. Not only was this Canadian knockoff novelty show her first professional role, but the Sailor Moon play would also prove to be a turning point in her personal life.

Coincidentally, there was another Canadian-born future Daily Show correspondent in the cast of Sailor Moon – the role of Tuxedo Mask was played by Jason Jones on the B team of this unlicensed fanfic, and it was during this production that Samantha met the man who would first become her husband and later her castmate.

Samantha would say about the production, “there is no photographic evidence, and if there were, I would not provide it readily.” Sadly, we were unable to find photographic evidence of our own, but we sincerely hope the memory of Samantha Bee’s Sailor Moon is immortalized in the hearts of the greater Toronto area’s children.

Bee and Jones would marry five years after the closing of Sailor Moon, then in 2003, Samantha Bee joined Jon Stewart’s correspondence team, followed two years later by her husband. 

In 2002, on the other side of the border, a little two-person one-act play called Matt & Ben was about to open at the New York International Fringe Festival starring an up-and-coming stand up comedian named Vera Mindy Chokalingam, better known by her stage name of Mindy Kaling. 

The play was co-written and co-starred Mindy Kaling with her best friend from college, a playwright and actress named Brenda Withers (who later had a cameo in the “Booze Cruise” episode of The Office). Kaling and Withers played Ben Affleck and Matt Damon respectively in a satirical, fourth wall breaking story about two roommates and best friends in Massachusetts who receive a mysterious gift from the unknown when the screenplay for Good Will Hunting drops from the heavens onto their coffee table.


“Do you like apples?”

The show was a Waiting for Godot style absurdist comedy grounded by the surprisingly touching relationship journey between our two heroes. Kaling’s Ben Affleck is a loyal, stubborn, devil-may-care ladies’ man who butts heads with his best friend and creative partner, a sensitive, precocious, perfectionist Matt Damon expertly brought to life by Withers.

With the exception of a couple flashback scenes, the entire show takes place in the pair’s Sommerville apartment over the course of 24 hours. Matt and Ben argue over what to do with the script, which Damon believes was sent to them as a test from God à la Job. The dissonance between their distinct personalities and their differing approaches to storytelling cause tension as their friendship is tested by the supernatural script.

The show was a surprise hit in the 2002 New York International Fringe Festival, and it played a sold out run which earned Kaling and Withers that year’s award for “Best in Fringe.” It was even picked up for an Off-Broadway run the following year.

Two years after Matt & Ben became an independent theater classic, television producer Greg Daniels picked Mindy Kaling’s spec script off of the massive pile of mostly unread submissions by aspiring stars and made one of the best decisions in TV history by in hiring her as a writer-performer for his American adaptation of a little UK sitcom called The Office. Said Daniels about the comedian who would go on to write more episodes of the smash hit than anyone else on the project,  "She's very original ... If anything feels phony or lazy or passé, she'll pounce on it." 

Wikimedia Commons / Claire Leahy

My girl's wicked smaht

You sometimes wonder if the people who witness these pre-fame projects can sense that there is immeasurable greatness in front of them doing a Sailor Moon cosplay or yelling at “Matt Damon” for breaking a picture of “Casey Affleck”.

We’re certainly fortunate to have an original recording of Matt & Ben. It’s so fascinating to see comedy history with your own eyes, albeit through the grainiest camcorder lens 2002 had to offer. If you want to see another amazing pre-fame performance with even fewer pixels, check out this basically prehistoric footage of “Dratch & Fey”, Rachel Dratch and Tina Fey’s sketch show from their Second City Chicago days.

If you somehow are in possession of a recording of Samantha Bee’s Sailor Moon play, I am begging you to list your demands in the comments. Let’s talk.

Top Image: Be Gentlemen    Kodansha / Toei Animation

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