Lawyers have long served as the butt of many a joke. When attorneys try being the comedian, however, the results are a mixed bag. Legal writers often focus on successful courtroom jokes: The New York Times’ Adam Liptak has reported on the funniest Supreme Court justices, multiple scholars have analyzed humor in the Supreme Court, and legal reporters gather compilations of quips and one-liners. Yet, the Supreme Court’s own guidebook for lawyers actually warns against telling jokes: “Attempts at humor usually fall flat.”

The other side of courtroom humor has largely gone untold. It is a sordid and painful tale of joke catastrophes so bad they led to mistrials, courtroom defeats, malpractice charges, judicial resignations and even a prison term. Even successful courtroom humor is often of the “you had to be there” variety.

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What follows are the worst courtroom jokes of all time (they are more of the “wish you hadn’t been there” type). But this list is not merely the un-funniest of the un-funny. Each example in this rogue’s gallery combines bad jokes with poor judgment, usually with personal calamity as the result.

1. Zimmerman trial. The most recent high-profile joke disaster occurred at the kick-off to the Zimmerman trial, when defense attorney Donald West began his opening statement with a knock-knock joke:

Knock-knock. Who’s there? Zimmerman. Zimmerman who? OK, you’re good for the jury.

The joke flopped for good reason. For one thing, the joke is older than Trayvon Martin. It was frequently repeated during the O.J. Simpson trial. For another, opening a murder trial with stand-up comedy is in questionable taste. Harvard Professor Alan Dershowitz blasted the joke as so god-awful that Zimmerman should have demanded an immediate mistrial.

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But this joke was not merely un-funny and in poor taste. It also managed to slam its own audience, the jury. The joke’s premise is that everyone with any sense should know who George Zimmerman is. The joke thus directly insulted the jury, who were selected precisely because they didn’t know (much) about Zimmerman. This joke demands that the jurors laugh at themselves for being ignorant.

Nevertheless, just as seasoned stand-up comedians can recover from a groaner, so too Zimmerman’s defense team managed to win back their audience. (The Zimmerman trial began with a joke and ended by becoming one.) Other legal eagles haven’t been so lucky.

2. Roe v. Wade. The title of Worst Joke in Legal History belongs to one of history’s highest-profile cases.

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Defending Texas’s abortion restrictions before the Supreme Court, attorney Mr. Jay Floyd decided to open oral argument with a sexist joke. Arguing against two female attorneys, Floyd begins: “It’s an old joke, but when a man argues against two beautiful ladies like this, they are going to have the last word.” The joke is demeaning and (as Floyd himself admits) unoriginal, but it also lacks the saving grace of at least being funny. A recording of the oral argument, which can be listened to here, demonstrates just how badly the joke bombed with the Supreme Court. Painful silence endures for just over three seconds. Not captured on the recording are the physical reactions of the justices. According to the later recollection of one of the “beautiful ladies” arguing against Floyd, Chief Justice Warren Burger was so furious that he almost rushed down “right off the bench at him. He glared him down.”

Dr. Ryan Malphurs, a scholar of Supreme Court humor (yes, there is such a thing), describes how “Floyd struggled to gain momentum through the rest of his argument.” A flustered Floyd responds to Justice Thurgood Marshall’s questioning with the stunning admission that these are “unanswerable questions,” a response that earns derisive laughter. (Thurgood Marshall replies, “I appreciate it.”) Floyd apologizes for his “artless statement,” which garners even more laughter. The man who had attempted to begin with a joke ends as the object of comedy. When the Supreme Court requested re-argument on Roe v. Wade eleven months later, Floyd was gone.

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Floyd’s disastrous “beautiful ladies get the last word” is the greatest failed joke in U.S. legal history, and some claim it is the worst joke of all time, in any setting. It occurred on the highest possible stage, in a high-profile case, while also (here’s the spoiled icing on the collapsed cake) managing to be a sexist joke during a landmark women’s rights case.

But did the failed Roe v. Wade joke actually affect the Court’s eventual 7-2 ruling? This seems highly unlikely. The only justice who conceivably could have been affected by Floyd’s argument was Chief Justice Burger. Burger was a conservative who later voted to restrict abortions – and yet he voted with the Roe v. Wade majority. So was Burger swayed to vote for abortion rights based on Floyd’s calamitous oral argument? Probably not – most scholars have explained Burger’s vote in Roe as a simple strategic move. (So long as he voted with the majority, Burger, as Chief Justice, could control who wrote the majority opinion in Roe, and thus partially control what that opinion said.)

There are, however, plenty of cases where the joke changed the outcome.

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3. Haluck v. Ricoh Electronics, Inc. In this employment discrimination case, the defense attorney’s comedy act resulted in the loss of a jury verdict in his favor. After one plaintiff testified that being fired left him feeling like he was trapped in a white, windowless room with no exits, the defense attorney, Mr. Callahan, began this cross-examination:

Mr. Callahan: Have you ever heard of The Twilight Zone? Witness: Yes sir. Mr. Callahan: Goes kind of like this, do do, do do. . . . You’re traveling through another dimension, a dimension not only of sight and sound, but of mind, a journey into a wondrous land, whose boundaries are that of imagination; that’s a sign post up ahead, your next stop, The Twilight Zone. Do do, do do. Do do, do do.

This last part was delivered in song. The judge, not the defense attorney, finally explained the point of Mr. Callahan’s “questioning” by asking the witness if his description of a white windowless room was inspired by the opening credits of The Twilight Zone. From this question came the following exchange, surely among the strangest in U.S. legal history:

Witness: No sir. Mr. Callahan: Do do, do do. Do do, do do.

The plaintiff’s attorney pleaded with the court to order Mr. Callahan to “stop singing.” The singing, however, was only one small part of a trial so absurd that it seems like a Twilight Zone episode. At one point, the judge announced that “we’re going to the soccer method here,” whereupon he began issuing “red cards” whenever he disagreed with the plaintiff’s legal objections. At another point, the judge fashioned a handmade sign reading “overruled,” creating a courtroom version of the judges’ paddles on Dancing with the Stars. The next day, defense attorney Mr. Callahan joined in this game, bringing his own, “much nicer version” of the overruled paddle for the judge to use.

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Amazingly, Mr. Callahan won the 30-day jury trial, but an appellate court threw out the verdict, calling the entire thing a “circus,” adding that “a courtroom is not the Improv.” “We can only imagine what was in the juror’s minds as they endured [this],” the appellate court scolded. The appellate court ordered the defendant company to pay plaintiff’s legal costs in appealing the verdict, and tossed out the jury verdict in the defendant’s favor, thus requiring a lengthy and expensive new trial before a different (and less friendly) judge.

4. Glickman v. Wileman Brothers & Elliot. In this case, longtime legal writer Tony Mauro blames a disjointed and joke-ridden oral argument for a 5-4 loss in front of the Supreme Court. Supposedly arguing that the government should not be permitted to force companies to pay for ad campaigns, attorney Thomas Campagne made several bungled attempts at humor, such as urging Justice Antonin Scalia not to buy green plums because “you don’t want to give your wife diarrhea,” and announcing that “We’re not going to advertise to people and change our message that we want you to eat worms.” Campagne’s legal arguments were as much a non-sequitur as his jokes. Various justices warned Campagne that “if you want to make a point, make it so that we can all understand it,” and, “I don’t understand what it is you say . . . it is not clear to me.” Mauro highlighted Campagne’s strange diarrhea jokes in criticizing him for “bathroom humor” that lost a winnable case. According to Mauro, a different style of argument would have “fared better – at least one vote better, which is all Campagne needed to win 5-4 instead of losing 5-4.” One of Campagne’s clients sued him for legal malpractice (even before the Supreme Court ruled on the case), describing Campagne’s oral argument as “my worst nightmare.” (The lawsuit settled.)

5. The joke that led to a jail sentence. While getting hit with a malpractice suit on top of losing a case in front of the most powerful court in the land may seem like the height of courtroom disasters, there have been worse. In at least one instance, a disastrous joke unquestionably led to a jail sentence. Once again, bathroom humor was at fault – this time literally. Using the bathroom during a courtroom break, one defendant noticed a juror at the urinal and jokingly announced, “Vote for me!” The juror reported the joke to the judge, leading to additional criminal charges, and an eventual conviction for attempting to influence a juror. The Third Appellate District of the Court of Appeals affirmed the decision, noting in a lengthy analysis that even if the juror believed the “defendant was trying to be funny,” the defendant may have “simultaneously intended” to influence the vote. Far funnier than the original joke is the deadpan concurrence by a member of the Court of Appeals: “[F]rom where I sit I cannot help believe that what appears to have been a stupid off-the-cuff remark tossed out by defendant on the spur of the moment in the men’s room did not justify the expenditure of prosecutorial and judicial resources that have now been devoted to it.”

6. The jokes that led to a death sentence. Has anyone really been sentenced to death as the result of bad jokes? Incredibly, some convicts claim the answer is yes. In one California death penalty case, the judge joked that any jurors caught discussing the case inappropriately would be shot. The convict claimed on appeal that this joke diminished the seriousness of the death penalty in the juror’s minds. (To be fair, by the same logic, the joke also diminished the seriousness of the defendant’s murders.)

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In another case, a death row inmate pointed to a joking exchange between defense counsel and the judge. One defense attorney was attempting to describe a hypothetical scenario in which he shot another defense attorney: “…if I were now to harm, shoot someone, Mr. Strople here, if I shot him right now—”

COURT: Permission granted. DEFENSE ATTORNEY: That might be justified— COURT: Mr. Strople is a public defender, for the record.

On appeal, the death row inmate claimed that this joke revealed the judge was biased against defense attorneys (because it is “justified” to shoot them). The appellate court agreed that the jokes were “unfortunate,” but rejected a new trial, calling the jokes “relatively brief and mild,” and noting that the defense attorneys themselves participated.

7. The joke about domestic violence. If anything is more inappropriate than joking about murder during a murder trial, it may be joking about domestic violence during a domestic violence hearing. One Minnesota judge resigned from the bench shortly after making this joke during a hearing about an order of protection (for spousal violence): “I’ve been married 45 years. We’ve never considered divorce, a few times murder maybe.”

8. The repeat offender. The all-time champion of inappropriate courtroom humor appears to a former judge in Maryland, Bruce Lamdin, who behaved like a meaner version of Michael Scott, the boss from The Office. Lamdin was suspended thirty days without pay in 2008 for rude jokes, including telling motorists from Pennsylvania, “What’s the big rush to get back to Pennsylvania? It’s an ugly state.” When a landlord testified that her tenant’s child had called her a bitch, the judge retorted, “I’m sure that wasn’t the first time someone called you a bitch.” Responding to a mother with a crying baby, he declared: “If she only knew how much I hate kids, she would not have brought that kid in here today.” Riffing on his child-hatred theme, Lamdin then mused to his courtroom that “we [already] confiscate cell phones and we put the cell phones in plastic bags and send them down to Annapolis. I suggested maybe we ought to do the same with children except poke holes in the bag. . . . We ordered some plastic bags about five feet tall but they haven’t been – they haven’t come in yet.”

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When a man with the last name Crook pled guilty to driving without a license and possessing drug paraphernalia, the judge demanded, “Why did you drive so poorly? Smoke a little weed before you got behind the wheel? . . . Smoke a little crack before you got behind the wheel? . . . Well, you’ve got the appropriate last name… All right crack head, Crook.” In a court hearing on prostitution, Lamdin performed an imitation of ghetto-talk. (The transcript reads much like when The Office’s Michael Scott got in trouble for reenacting a racially-charged Chris Rock routine.) “Who put up your bond money for you, your pimp? . . . If I were to release you, you’d be scratching that itch tonight. . . . Ma’am, you can’t bullshit a bullshitter.”

Although the Maryland Commission on Judicial Disabilities suspended Judge Lamdin for inappropriate language, one gets the sense that the Commission was especially offended by jokes directed at them. The opinion quotes Lamdin criticizing the Circuit Court, “I mean, they don’t work in the afternoon up there. . . . They’re all on their way to have cocktails or something up there at the Circuit Court. Yeah, they don’t work in the afternoon. Who are they kidding?”

The Commission also criticizes him for accusing prison guards of corruption and courts of indifference: “You may be able to get some crack down there. . . . Those guards there provide services for services. . . . They don’t care about prostitution in Baltimore City. They’ll move her into one of the diversion courts, spank her, and send her on her way. . . . They treat prostitution like spitting on the sidewalk. . . and you’re guaranteed to have it dismissed when you go up to the Circuit Court.” The Commission declared: “Criticism of judicial colleagues, particularly from the bench in the courtroom, hardly leads to trust and confidence by the public in the Judiciary.” Lamdin would later retire after audio emerged of him degrading a victim of domestic violence.

Considering the squalid history of failed legal humor – lost cases, malpractice claims, resignations, and imprisonment – perhaps lawyers should be happy that they are usually just the butt of jokes, and not the ones telling them. Otherwise they might – like the singing Twilight Zone attorney – step into some deep “do do, do do.”