Parks and Recreation followed a group of zany characters in a small town in Southern Indiana and centered on the group who worked in the parks department. Although the show centered on the small group, there were countless side-characters that were just as hilarious as the main cast.
Jean-Ralphio Saperstein, portrayed by Ben Schwartz, was a fan-favorite reoccurring character who showed up as one of Tom's friends and frequent business partner. Most of his dialogue is quick, comes out of nowhere, and outrageous which makes it all the funnier. Here are some of Jean-Ralphio's funniest quotes throughout the show.
"Why don't you turn that frizzown upsidizzity."
This line is so in character for Jean-Ralphio as he tries to cheer up his friend by telling him to turn his frown upside down, but he can't simply say that and has to add some flair to it.
The line doesn't cheer Tom up, but unsurprisingly and hilariously he also doesn't call attention to Jean-Ralphio's flourish either.
"You just missed the craziest of crazies..."
Ron.
Jean-Ralphio comes in and breathlessly describes his night by saying that Tom just missed "the craziest of crazies: clubs, girls, dancing, naked, mom, argument, police, fleeing the scene, hiding in a dumpster, coming here and crashing on your couch for a week 'cause technically I'm homeless" before he flops back onto Tom's couch and falls asleep immediately.
"Guess who's got two thumbs and was just cleared from insurance fraud? This guy!"
When Ron refuses Chris's job offer Jean-Ralphio pops up behind the two and immediately says he's in to take the job. He also shares that he was just cleared from committing insurance fraud so he's ready to work whatever the job is.
Chris turns him down and says, of course, there's no job for him there and Jean-Ralphio agrees that that's probably the smart move.
"Your eyes are about to piss tears."
Jean-Ralphio and Tom are in charge of the beloved Li'l Sebastian's memorial and he says this line with all the confidence in the world before he starts the memorial video.
Donna is the only one that hears it and calls him nasty for saying it. As usual, he's completely undeterred by Donna's criticism and he's just as ready to start the video as he was before the line.
"I'm so alone."
Jean-Ralphio says this quick hilarious, but sad, line at the end of one of the most iconic episodes of the show. After all the characters have gotten drunk off of snake juice they all crowd into Donna's Mercedes because she's the only sober one and agrees to give them all a ride home.
They're all drunkenly laughing at a joke and then Jean-Ralphio says this line when everyone stops laughing. The line throws the viewer off as a different type of comedy from the character and, unfortunately, the Parks and Recreation special showed that Jean-Ralphio is just as alone as ever.
"Why don't you live your life like that cow from the video?"
Jean-Ralphio and Tom are put in charge of the memorial for Li'l Sebastian and Tom is debating whether or not to leave his job at the parks department to start a business with his friend.
Jean-Ralphio has some words of wisdom for him and tells him to live his life like the cow in the video. Tom responds that Li'l Sebastian was a horse and Jean-Ralphio says yeah because he followed his dreams. It's a hilarious, nonsensical, and strangely optimistic line.
"I heard sack of flour and high school. Are you ding-dongs makin' fake drugs for Sophomores because if true, this guy wants in."
Jean-Ralphio pops up behind Chris and Ben when they're talking about parenting and he responds with this line. It's a very specific image that makes the audience wonder if he's done this before, or if someone did this to him when he was a sophomore in high school.
Either way, it's a hilarious, pretty outrageous, and extremely specific image that could only come from Jean-Ralphio.
"That's too much responsibility. I've gotta find a way out of this."
When Tom thinks Mona-Lisa might be pregnant he goes to her to ask if it's true and talk about what they should for the baby. Jean-Ralphio is in on the conversation, for some reason, and immediately starts to panic at the prospect that he could be an uncle soon.
He gets serious for a moment and then becomes wildly happy when Mona-Lisa reveals that there's no possible way she could get pregnant and he snaps back to normal.
"The wo-o-o-o-o-o-o-rst."
In a town of outrageous characters, Jean-Ralphio always stood out in Pawnee as one of the most obnoxious characters, but then the show introduced his twin sister Mona-Lisa, played by Jenny Slate.
Jean-Ralphio describes her as the worst, in his go-to singsong voice, and Mona-Lisa is hilariously just like her brother.
"I made money the old fashioned way. I got run over by a Lexus."
Jean-Ralphio has been caught up in a lot of schemes, mainly insurance fraud, throughout the series and this is one of his funnier lines about it.
He's a character that mainly lives off his family's wealth and from scheme to scheme without ever really holding onto a real job. The fact that he refers to his insurance fraud as making money "the old fashioned way" is very in character for him.