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Top 30 Craziest Judge Judy Cases EVER

Top 30 Craziest Judge Judy Cases EVER
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VOICE OVER: Phoebe de Jeu WRITTEN BY: Joe Shetina
Order in the court — things are about to get wild! Join us as we count down the most jaw-dropping, outrageous, and unforgettable cases ever brought before America's favorite no-nonsense TV judge. From Tupperware attacks to fake cases, bleached clothes to boiling water, Judge Judy has seen it all — and she's not afraid to say exactly what she thinks! Our countdown includes cases like the infamous Grindr lawsuit, the Tupperware attack demonstration, the deer crash sisters, the shocking fake case exposed by Vice, and the heartbreaking case of a woman suing a grieving mother. Which Judge Judy case do you keep coming back to? Let us know in the comments below!

#30: The Worst Apartment Ever

The plaintiff in this case was one of several tenants in a large house, and she’s come to Judge Judy for the return of rent and security deposit. But her reason is fairly novel, even for this show. She witnessed one roommate murder another. Despite only being there for a month, the plaintiff is forced to sue the landlord for her security deposit. Adding to the bizarre nature of this case is the landlord’s behavior. His blank stare as the judge speaks seems to suggest that he has no idea why he owes her anything. The plaintiff’s story is harrowing, and luckily, Judge Sheindlin doesn’t make her retell it in detail.


#29: Holding the Door

Politeness and common sense may be in short supply, but it’s nothing to get into a fistfight over. The litigants in this case were customers at the same restaurant. When defendant Karl Pogue held the door open for his wife and children, plaintiff You You Xue zoomed past them. That’s all it took for a grudge to be born. The crazy thing is Judge Sheindlin appears to be on the defendant’s side—until, of course, he admits to going back into the restaurant to approach the plaintiff. Then it’s a whole new story. Imagine getting this upset over a minor social faux pas.


#28: Forcing Him Out

The plaintiff alleges he and the defendant, his ex, lived together. However, she filed an order of protection that precluded him from being in the house they co-owned. Once Judge Judy starts digging into the case, the defendant doesn’t respond to the facts or her questions so much as she begins trying to bury the plaintiff in heinous allegations. Regardless of what’s true or not, she feels entitled to the house. Unfortunately, she can’t wait her turn. She spews a stream of hatred that only stops when the judge throws her out. The melodrama continues even after the case is thrown out, with both individuals offering more details that sound more like a soap opera than real life.


#27: Harassing the Landlord

Maybe the Internet was a mistake. Six young men lived together in a house owned by plaintiff Mary Class until she exercised her legal right to end their lease. Not only did defendant Steven Reid not leave in time, he launched a crude, obscene, and degrading harassment campaign against Class. His methods included posting a personal ad on Craigslist in her name. As Reid’s friends, former roommates, and witnesses sit by and watch, we get to see in real time as they learn about some of what went on behind their backs. Whether his friends knew or not, it’s clear they all have some shame about it.


#26: Making up Stories

In this case, the plaintiff’s eyes do as much talking as her mouth does. Her reaction to the judge’s assertion that there may have been a romantic angle to her relationship with the defendant is almost operatic. If silent movies were still a thing, she’d be a star. But regarding the borrowed TV she’s suing for, the judge insists her entire story doesn’t make sense unless there was more to it than she’s willing to admit. Whether it was a friend breakup or a regular breakup, it’s a wild ride. Competing versions of events and the plaintiff’s confused testimony make this one particularly thorny, overdramatic, and genuinely hilarious.


#25: Not a Good Example

From the jump, defendant Heather Ramsdell’s story just makes no sense. She didn’t hit the plaintiff’s car, but she did stop and get out of her car to talk to her. She didn’t make the scratch on the plaintiff’s car, but she offered to buff out the scratch even though she had nothing to do with it. And if the judge needs proof, her young son is willing to testify on her behalf. Judge Sheindlin smells a rat right away. She begins to shame the defendant for lying in front of her son, who looks terrified the moment the judge speaks to him.


#24: Busting Down the Door

Lisa Palma busted down her tenant’s door, made threats on video, and gave the judge plenty of attitude. The craziest thing is she’s actually the plaintiff in this case. She rented a room to defendant Tiffany Colon. Palma became upset when she realized that Colon was moving out without notice, which was legal under her lease. The judge figures out what happened almost immediately. But she doesn’t need much more evidence than video of Palma busting in Colon’s door and knocking her phone out of her hand. When the plaintiff doesn’t seem to get the point, Judge Sheindlin plays the video again for her millions of viewers.


#23: Fighting Her Sister’s Battles

A schoolyard scrap between high schoolers is unfortunate, but it’s not all that unusual. This one was especially unhinged because only one of the defendants is high school aged. Apparently, an adult sister got involved in the fracas. The case takes a turn for the worse when the defendants’ clearly hopeless and detached mother begins to speak on her daughters’ behavior. She’s not exactly a stellar witness for the defense. When the judge says the adult daughter needs to be arrested and her own children put in foster care, the mother just nods in agreement. It paints a pretty bleak picture.


#22: An Ex to Forget

If there were allegations that you were behaving in a violent and disturbed manner, you’d think you would at least clean up your act for court. Defendant Sabrina Perez can’t even control her face when the plaintiff is speaking. But given her in-court behavior and the mounting evidence, his allegations that she vandalized his car and stalked him appear more and more probable. Perez boasts about weaseling her way into his life through his friends, admitting to sleeping with one of them right in court for no real reason. She throws everything at the wall to see what sticks, including an impossible pregnancy with the plaintiff. But Judge Judy isn’t buying. This case is already sounding too much like a bad movie.


#21: A Measured Response

Out of the blue, Valencia Carroll asked her mother and stepfather to watch her friend’s infant for an undetermined amount of time. The audacity is already off the charts. Immediately, she can’t get her story straight for the judge. The amount of lying she’s doing from the jump is almost impressive, but she’s a cool customer—not that Judge Judy is fooled. Carroll’s parents did the sensible thing and declined to take in someone else’s baby. Having already demonstrated an interesting sense of logic and reason, it’s no surprise that Carroll’s response was unreasonable. She broke their television and vandalized her stepfather’s car.


#20: The Mother-in-Law from…

In what plays like a particularly unhinged sitcom, the plaintiff in this case, Patricia Reynante, is a disgruntled mother-in-law who just doesn’t get the hint. Ms. Reynante’s ongoing acrimony with the defendant, her son’s ex and the mother of her grandchild, led to a restraining order against her. The judge knows going in that she probably deserved it. Her interruptions and defensiveness get pretty tiring pretty fast, but it’s her complete lack of accountability for breaking a restraining order that really takes the cake. If there’s one thing Judge Judy has no patience for, it’s people who flagrantly ignore the law.


#19: The Interrupter

Kim Knowler is suing Thomas Dougherty after he tried to cancel a reservation at her motorcycle rental business. Though the charges were eventually reversed, the plaintiff is here to collect for fees incurred. But the judge finds her business practices pretty harsh. Even as the judge tries to talk to her, she keeps repeating herself as if talking over the judge is going to change her mind. The plaintiff just keeps repeating, “No refunds.” Maybe she thinks it’s like a spell. If you repeat it enough times, it comes true. That’s not how things work in Judge Judy’s courtroom.


#18: Why Are You Laughing?

Judge Judy hears a case about a man who threw a bottle at someone’s car. He readily admits he threw the offending bottle, but still can’t understand how he did the damage. Pretty standard stuff at first. But as the suspiciously spacey and red-faced defendant tries his best to keep it together in court, he can’t even keep from laughing through the case. The judge can hardly believe he thinks any of this is funny. She tells him that he’s “the only fool” laughing. What’s hilarious is everyone in the courtroom is definitely trying not to laugh the whole time.


#17: Your Honor, That Child is a Liar!

At least, that’s what this defendant wants the judge to believe. As the sweet, soft-spoken little boy who was bitten by her dog gives his testimony, defendant Lourdes Rodriguez can’t help but point out the factual inaccuracies. Not the best way to endear yourself to anyone, let alone the judge. The judge quickly deduces that she has a pre-prepared version of the events that not only makes her look better but also completely contradicts her sworn statement. The fact that this woman is so willing to throw this child under the bus, and even blame him for it, is kind of reprehensible.


#16: Bleaching His Clothes

A couple’s spat turns into a destruction of property case, with the plaintiff’s clothes covered in bleach. The defendant blames the plaintiff for most of the damage for grabbing the bottle of bleach out of her hand as she was pouring it. Her arrogance with the judge is clear from the jump. Even after she is reminded she’s not on “Jerry Springer,” the defendant can’t help herself. The judge rules against her and dismisses her counterclaim, and that’s when the defendant loses it. Her behavior is so wild that the judge is compelled to come back out and let her have it. Although there are probably a lot of people who sympathize with her, the judge deals with the law, not morality.


#15: Case Dismissed… Nevermind

Litigants rarely get a second chance in Judge Judy’s courtroom. A man accused of stealing a television and assaulting his own sister sues his mother for false arrest. However, he storms out after the judge asks about his previous arrest record. In a rare show of mercy, she allows him to retry the case after his outburst. Things don’t go that well in the second round either. Through slurred speech, the plaintiff can barely contain his temper. His mother can barely look at him throughout the case, and given that the daughter involved in the dispute has recently died, it’s a tragic and unnecessary situation.


#14: A $5,000 Haircut

When Judge Judy actually bothers with your case just for the pure entertainment of it, you know you’re in trouble. The plaintiff told the judge not to hold his occupation as a lawyer against him. In her brilliantly incisive way, she tells him it’s not his profession that offends her, it’s his stupid lawsuit. The plaintiff, who is, let’s say, not exactly Fabio when it comes to his hair, is suing a hairstylist who cut his hair too short. So, he’s suing for $5,000. The fact that he seems completely earnest in his lawsuit is even weirder. Judge Judy is a good sport, though. She refunds him the $10 he paid for the cut and sends him on his way.


#13: Broken Toilet

Accidents happen, but suing a friend over something that not only wasn’t their fault, but is supremely embarrassing is lowkey evil. Judge Judy is rolling her eyes ten seconds into the case, and we get the feeling she already knows how this is going to go. Though the plaintiff insists her friend broke the toilet and is responsible, the judge is less than impressed with how she handles the situation. What it amounts to is a plaintiff who’s a bad friend, trying to get money and embarrass her ex-friend. At least we hope they’re ex-friends. The good-natured defendant can definitely do better.


#12: Judge Judy Learns About Grindr

We never thought we’d see the day when Judge Judy would learn what Grindr was. However, her reaction is exactly what we would’ve thought if she ever did. The plaintiff in this case, an older man, and the defendant, a noticeably younger man, met on an app. The lawsuit is, unsurprisingly, about unpaid loans. Judge Judy wanted more information. This leads to a thorough explanation of the dating app, Grindr. Although she looks incredibly confused, some of the audience members clearly know what’s up. She eventually clicks right back into the case. She knows exactly what kind of social and financial arrangement the two had. However, her initial response to the idea that the defendant was just making friends on the app is priceless.


#11: 10 Kids, Zero Brains

The “Judge Judy” courtroom is not the place to advance your standup career. You will end up looking like a fool. Danny Gonzalez didn’t need the judge’s help to do that though. When the judge expresses some surprise at the 21-year-old having 10 children, he responds by making a vulgar, if somewhat nonsensical joke about the judge’s daughter. The most pathetic thing is that he really does look terrified, but stupidity overrode his good sense. Despite Gonzalez’s obnoxious behavior, it’s actually one of Judge Judy’s tamer moments. Without even raising her voice, she puts him squarely in his place.


#10: Allow Me to Demonstrate

Dr. Noel Howell is probably a legend on the dance floor. The thing is Judge Judy doesn’t have a dance floor. That didn’t stop him from doing an incredibly unfortunate, but now-legendary reenactment of the plaintiff’s drunken antics while on the job. During a movie shoot in the Caribbean, Dr. Howell alleges that the plaintiff was smoking “the good Antigua Ganja” and things quickly got out of hand. His description of her increasingly erratic behavior is endlessly memeable, but his imitation of her dancing and screeching while under the influence is an unforgettable courtroom moment.


#9: Doused with Boiling Water

What starts as an incredibly upsetting and violent case about a roommate squabble that led to the plaintiff being attacked with boiling water turned incredibly sad by the end. Judge Judy quickly sussed out that the litigants were high during the event. Despite the plaintiff’s bizarre assertion that the police officer who responded to the scene was “fugazi,” the judge soon realizes she is in desperate need of care for a drug addiction. Instead of adding insult to injury, the judge actually takes great care to explain why the police didn’t act on her initial report. She was simply too deeply under the influence to advocate for herself.


#8: Push

Look. We get it. It’s embarrassing to be kicked out of the courtroom, especially if you’re not the first, but the second person in your group to go. Because that shows that you just can’t listen, and Judy has no time for the likes of you. The defendant — not willing to let well enough alone — had the audacity to talk back to Judy on his way out, then turned to storm through the doors that... wouldn’t open for him. Forget embarrassed, this is outright humiliation at this point. As he shrugs his shoulders to ask, “How do I get out,” you can hear him being told to push, not pull.


#7: For Mature Audiences

We’re not judging anyone for their chosen profession — and neither is Judy, for that matter. You just might... have to... explain it to her. Such was the case when the plaintiff had to explain her adult novelty party business to Judy, who was able to connect the dots when told about the lotions and, more specifically, vibrators. This leads to the plaintiff listing off the names of every item that went missing, both Judy and her bailiff, Bernard, expressing various levels of huh as if trying to figure out what everything is. Then, the sex b-bomb is dropped: one of the items was returned used. Poor, poor Judy.


#6: The Fake Case

There’s always debate on whether or not the cases we see in any televised courtroom drama are real. While the jury will always and forever be out on that one, we can say, with utmost certainty, that this particular case is an absolute work of fiction. In an interview with Vice in 2014, it’s revealed that the case about smashed TVs and the tragic death of a cat was made up purely for the settlement money and free trip to L.A. There was no fight and, thankfully, no dead cat. While it’ll definitely make us question the validity of a case, the defendant did, at least, confirm that Judy really is that intimidating in real life.


#5: Dumb & Dumber

If you’re going to say you didn’t steal a purse, you might not want to tell a judge what was and what wasn’t in the purse you definitely did not steal. As the plaintiff lists the items in the purse in question, one of the accused defendants insists there was no earpiece. If only every case were this easy to prove. Before they can even realize what’s happened, Judge Judy has ruled against them and the two have become a laughing stock in front of millions. We don’t know if this was the shortest case ever featured on the show, but it has to be in the running.


#4: Tupperware Attack

Judge Judy always looks like she’s seen some things, that being said, there are times when a plaintiff says something so unbelievable that she, as they say, can’t even. When a plaintiff tells her that the defendant threw not just one, or two, but all of the Tupperware on her — not at her — Judy calmly says, “She didn’t throw all of her Tupperware on you.” Oh, yee of little faith, because the plaintiff not only insists that it happened, she gives a live demonstration, complete with aggressive voice acting, a lot of finger-pointing, and scrunched-up faces. At least the Tupperware wasn’t full of food? Or that last lady's... lotions?


#3: Loserds

If you haven’t figured it out by now, some of the guests on Judge Judy aren’t exactly what you’d call the sharpest tools in the shed. Case in point, when our next defendant came to plead her case over an assault charge, Judge Judy quickly demands to know why they were swearing at the plaintiff. Her answer, while not only provoking a court-wide groan for butchering the word ‘losers,’ actually demonstrates that she initiated the conflict with the defendant, securing Judge Judy’s decision almost immediately. Next time you want to accuse someone of assault, maybe make sure you’re not actually the one who initiated it.


#2: Venison Will Get You Nowhere

When will people learn that you have to get permission before you take something from someone else, even if you, supposedly, take it all the time? In yet another case of “I’m always able to borrow the thing,” two sisters find themselves in court over damage done to a car. The defendant got into a wreck with her sister’s car, crashing into a deer, but since she takes the car all the time and has “helped her sister sometimes” she thinks she should be in the clear. At least she was nice enough to offer some of the deer. Yes, the deer she hit. With her sister’s car. Yeah... you’re still gonna have to pay back that $1,300.


#1: Suing a Grieving Mother

In what is absolutely the craziest, and possibly the most morally unconscionable case in the history of the show, a woman sues a grieving mother for damages to her car. The car was damaged when her son, whom she allowed to drive her car, gave the defendant’s daughter the keys to drive it. Defendant Nelda Bailey’s daughter was killed in an accident, and now plaintiff Wendy Moore is suing. Moore is so cool about it that it’s actually disturbing. She’s convinced she’s in the right. In fact, she blames the defendant’s deceased daughter for the whole thing. The audience applauded when Judge Judy verbally destroyed her and ruled in favor of the defendant, granting her the $5,000 she was suing for.


Which “Judge Judy” cases do you keep coming back to? Sound off in the comments.

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