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Jean-Ralphio and Mona-Lisa Saperstein's Best Moments from Parks and Rec

The duo was responsible for some of the hardest laughs in the iconic comedy series.

By Jessica White

Parks and Recreation is a sitcom masterpiece, largely thanks to the powerhouse comedians in its cast. Fans of the NBC series have fallen in love with the residents of Pawnee, but many agree the Saperstein siblings were certified show-stealers. 

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Watch every episode of Parks and Recreation on Peacock.

The duo — consisting of party animals Jean-Ralphio (Ben Schwartz) and Mona-Lisa Saperstein (Jenny Slate) — never failed to bring constant laughs with each guest appearance on Parks and Rec. Jean-Ralphio was the best friend and "business partner forever" to Tom Haverford (Aziz Ansari), frequently orbiting the office to swoop in on any questionable investment opportunity. If Jean-Ralphio needed backup on a scam or scheme, he could always call Mona-Lisa, his equally eccentric sister, to provide hilarious intel and disinterested support.

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And if the Sapersteins were on the prowl, ridiculous raps and needless singing were on the horizon.

Below, relive some of Jean-Ralphio and Mona-Lisa's most hilarious moments on Parks and Rec. 

Jean-Ralphio's Ridiculous Parks and Rec Introduction

Jean-Ralphio's introduction in Season 2, Episode 13 ("The Set Up") was the perfect tee-up for what would become a beloved recurring character. After Ron Swanson (Nick Offerman) needed a new assistant, Tom pitched Jean-Ralphio for the gig.

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When asked why he'd made a good assistant, Jean-Ralphio declared, "For starters, access to the illest clubs, and that's just for starters. I will work for you. I'll be on you 24/7. I'll be like your family. I'll be here when you get here in the morning. Soon enough, I'll be there to tuck you into bed at night. Don't worry, it's not gay. Do we have any questions?"

Needless to say, Ron wasn't interested. But Jean-Ralphio's presence in the department was far from over. 

Jean-Ralphio's Rap Artistry

Nick Offerman as Ron Swanson stands in front of and Ben Schwartz who speaks into his ear

Some of Jean-Ralphio's most iconic moments occurred in Season 3, Episode 13 ("The Fight"). After Tom and Jean-Ralphio invested in the Snakehole Lounge, they decided to debut a new liquor called Snake Juice to get people to the club. Snake Juice ended up being the downfall of many of our Parks and Rec fan favorites, but rest assured, Jean-Ralphio was there to check in with a personalized rap.

Sadly, these raps always started strong but fell flat. 

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“K to the N to the O-P-E! She’s the dopest little shorty in all Pawnee... Indiana," he quipped to Leslie Knope (Amy Poehler). Later in the night, he also gave Ron his own personalized ditty: “R to the O to the N-N, I said Swanson got swagger the size of Big Ben… clock.” 

What was the source of Jean-Ralphio's money?

Tom valued Jean-Ralphio as a business partner partially for his mysterious supply of capital, leading to many sporadic investments throughout the series.

But how did JeanRalphio make this money? It was certainly not by working. In Season 3, Episode 16 ("Lil' Sebastian"), he gave us a bit of a clue while brainstorming investment ideas. 

"I made my money the old-fashioned way," Jean-Ralphio bragged before bursting into song. "I got run over by a Lexuuuus!"

Jean-Ralphio, Would-Be Lothario

Ben Schwartz as Jean-Ralphio Saperstein, Amy Poehler as Leslie Knope, and Aziz Ansari as Tom Haverford stand together

Part of Jean-Ralphio's charm was his total lack of it, despite his affinity for the ladies. While Jean-Ralphio would hit on everyone he met, from April Ludgate (Aubrey Plaza) to Chris Traeger (Rob Lowe), he had a soft spot for the lovely Donna (Retta). (Who doesn't?) That said, Donna always dodged Jean-Ralphio's advances, but each attempt delivered unbridled hilarity.

Case in point: When he tried to get Donna to agree to a date at the Snakehole Lounge in "The Fight."

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"Listen, beautiful. Let’s cut the bull, right? You want this, I definitely want this, T.H. wants this. Let's seal this devil's three-way right here, right now," Jean-Ralphio pitched. "Step one, We buy into this club. Step two, we roll over to the club, either in your Mercedes-Benz or my pre-owned Acura legend. Step three, I dagger you on the dance floor. Just bounce bounce bounce bounce, now all the ladies sing, bounce bounce bounce bounce bounce. What do you say?"

Jean-Ralphio as Tom's Roommate

Ben Schwartz as Jean-Ralphio Saperstein leans across a table

When Tom launched his idea for Rent-a-Swag in Season 5, Episode 6 ("Ben's Parents"), Ron helped Tom realize that Jean-Ralphio wasn't built for entrepreneurship. But whether or not he'd be a stable roommate was yet to be proven — that is, until he burst into Tom's apartment. 

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"Tommy T!" Jean-Ralphio yelled. "You just missed the craziest of crazies. Clubs. Girls. Dancing. Naked. Mom? Argument. Police. Fleeing the scene. Hiding in a dumpster. Coming here. Crashing on your couch for a week because technically I'm homeleeeeess."

The Mystery of Jean-Ralphio Solved: "Pills, Baby!"

Ben Schwartz as Jean-Ralphio Saperstein

Between his endless pestering and maniacal lifestyle, Jean-Ralphio soon became a core member of the Parks and Rec family. But that doesn't mean he wasn't obnoxious that entire time. The method to Jean-Ralphio's madness was boggling to most, leading Leslie to snap and straight up ask him what his problem was in Season 7, Episode 11 ("Two Funerals"). 

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"Why are you like this?!" Leslie exclaimed. 

"PILLS, BABY!" Jean-Ralphio sang with glee. 

Meet the Marvelous Mona-Lisa Saperstein

From the moment we first met Mona-Lisa in Season 5, Episode 16 ("Bailout"), there was something familiar about her. Whether it was her eccentric style or her bold introduction upon being hired by Tom for Rent-a-Swag, it was immediately clear Mona-Lisa was a little nuts. As soon as Ben (Adam Scott) learned her last name was Saperstein, his eyes widened with shock.

"Does that mean...?" he asked. 

"Oh, yeahhhh!" Jean-Ralphio sang, appearing out of thin air behind his shoulder. "She's my sister. My twin sister from the same mister." 

Jean-Ralphio continued by giving the skinny about his dear sibling, whom he loudly sang is "the worst person in the world."

Fans immediately fell in love with the endlessly entertaining "klepto, nympho, and pyro," Mona-Lisa, a comedic force of nature who managed to out-crazy her neurotic twin brother. 

Mona-Lisa's Tagline: "Money, please!"

Aziz Ansari as Tom Haverford, and Jenny Slate as Mona-Lisa Saperstein laughing together

Mona-Lisa might have hated working with every fiber of her existence, but she loved money. She asked for it at any given opportunity and refused to "F with poor-sies."

Unfortunately, Dr. Saperstein (Henry Winkler) spoiled Mona-Lisa and Jean-Ralphio recklessly, leading to a hilarious level of entitlement and a possible cause for their immaturity. 

Dr. Saperstein's Love for His Kids

Despite openly referring to Mona-Lisa and Jean-Ralphio as his "terrible children," Dr. Saperstein became a doormat anytime his kids entered a room — especially in Season 6, Episode 1 ("London").

After the Saperstein siblings lied about Rent-a-Swag being Jean-Ralphio's idea, Dr. Saperstein became dead-set on seeking revenge against Tom by starting a rival business.

Luckily, Tom managed to corner Jean-Ralphio and Mona-Lisa into a meeting with their father to admit their wrongdoings. Jean-Ralphio fessed up (in his own way), but Mona-Lisa held her ground. 

"I also have something to say," Mona-Lisa declared with mock earnestness. "I have done nothing wrong ever in my life." 

"I know this," her father nods. "And I love you."

"I love you too, Daddy," Mona-Lisa said before cutting the chase. "Money, please!"

Jean-Ralphio's Funeral and Life Insurance Scam with Mona-Lisa

Jenny Slate as Mona-Lisa Saperstein stands while speaking to a table of men

As Parks and Rec approached its series finale, many wondered where Jean-Ralphio and his wild sister would end up in life. After Leslie wished Jean-Ralphio a long and happy life in Season 7, Episode 12 ("One Last Ride"), we got a sneak peek at his life in 2022.

Cut to Jean-Ralphio's funeral, complete with a rousing arrangement of Lil Jon's "Bend Ova." This was an instant jaw-dropper, but luckily, the death turned out to be one of the Saperstein sibling's many scams. 

Jean-Ralphio, it was discovered, had staged his death so his sister could cash out on the life insurance policy and launch a casino in Tajikistan. True to form, they were busted after being spotted spying on the funeral.