Church: You want to give out the symbols of Olympic victory to losers? That doesn't sound much like you, Sarge. So what will it be? Gold, silver, bronze and... Sarge: Enriched uranium! The losers will be forced to wear radioactive isotopes, making sure they die the excruciatingly slow and painful death they deserve!
You're being given an award, but not for something you're proud of. In fact, it's for something of which you're very, very not proud and for which you certainly don't want an award.
There are two kinds of Medals of Dishonor:
The purposeful kind - The award is a joke specifically meant to make the recipient's life miserable, such as an "award" for "ugliest hair" or "tiniest brain". These can generally be treated in two manners.
The award is given publically and is meant to make the receiver a figure of ridicule.
The award is given by friends and colleagues as a form of good-natured ribbing.
The accidental kind - The award is honestly meant as an honor, but it isn't received as such. There are several possibilities here.
Smoker of One Piece is furious at the promotion given for Alabaster's salvation when it is the Straw Hat Pirates who were the country's saviors; his participation in it was negligible at best compared to even Tashigi. The Government was basically cornered at this point; either cover up the truth with this sham of a medal, or openly admit that Pirates saved a country from one of their own rogue privateers.
In Hannibal (book and film) Clarice Starling gets a letter from the Guinness Book of World Records congratulating her on being the female FBI agent who has shot and killed the most people.
Gran Torino: You wanna know what it's like to kill a man? Well it's goddamn awful, that's what it is. The only thing worse is getting a medal of valor for killing some kid who wanted to just give up that's all.
Apocalypse Now: They were gonna make me a major for this, and I wasn't even in their fucking army anymore.
In The Majestic the town received a statue to commemorate their contribution to the war effort and the soldiers who never returned. The loss was still too raw for the people, so the memorial was stored in a basement.
The Star Wars Expanded Universe novel Wraith Squadron has character Kell Tainer awarded with the Kalidor Crescent (an award recognizing conspicuous and simultaneous achievements in piloting skill and bravery) for the spectacular maneuver he pulled in an attempt to save his teammate Jesmin Ackbar. Kell inwardly doesn't agree to that and looks like he's going to throw up... because, well, the maneuver actually failed to save Jesmin at all and he was scared out his mind the whole time. Eventually, his friends coax him into realizing the fact that he made the attempt at all and didn't manage to crash his own bird qualified him, even if the lack of success was tragic.
The imperial medals given to pilots have tacky names. , , 
At the end of Iron Fist, Garik Loran was almost killed and managed to limp back with both his fighter and himself in horrible shape. Parts of him and his X-Wing were "intermingled". While recovering, he was presented with the Award of the Mechanic's Nightmare - a statuette of "a New Republic mechanic with wrench upraised as a weapon. The mechanic's expression was of pure, if silly, rage." He takes it in good cheer.
Face: "I want to thank everyone who retrieved pieces of me, everyone who retrieved pieces of my X-wing, and especially those who sorted them out correctly."
Also in line with this trope is a scene in a later book when two pilots, badly injured in the line of duty, mention after getting better that the squad didn't always show enough appreciation. In response, the Wraiths kinged them with scrap-metal crowns, gave them dowel rods with tassels as scepters, and threw brightly-colored rubbish as celebratory confetti.
Runt: "Do all kings have to suffer this?" Wes: "Well, any king with Face Loran as his majordomo." Face: "And now the two kings fight each other to the death, and we space the loser." Wes: "Try again." Face: "We space the winner?" Wes: "One more." Face: "We buy you a drink." Wes: "That's more like it."
A borderline example comes from yet another scene in the book involving a wounded pilot. Piggy killed an assassin coming after Admiral Ackbar and got shot doing it. After he exits the bacta tank for the last time, he finds his squad members waiting for him, with mild taunts ("We heard the new vintage of Piggy was being decanted") and gifts ("To remind you of your time spent here, we got you some things. Bacta flavored brandy, bacta flavored candy, bacta flavored cheese...")
Face "Runt and I worked up a little manual for you. It's called 'How to Duck'."
The X-Wing Series comics have Baron Fel, best Imperial pilot since Vader's death, put under the command of an incompetent admiral with terribly lax morals and no sense of strategy. He gives Fel and Fel's pilots medals (and gives us the page image), which Fel refuses because he thinks they didn't do anything worth accolades. They flew against Rebel pilots and, close to victory, were suddenly recalled by the admiral when the man saw reports of X-Wings too close for comfort and wanted the protection of his entire force. Fel's pilots accept at the ceremony, and we◊ see◊ that the "starburst" medals were designed by the admiral and are really ugly. Thus, they fall under all three of the "accidental" categories.
Colonel Cathcart: "What can we give him a medal for?" Colonel Korn: "For going around twice. You know, that might be the answer - to act boastfully about something we ought to be ashamed of. That's a trick that never seems to fail."
In Cetaganda, Miles is awarded the Cetagandan Order of Merit, the highest honor given by The Empire that is his planet's arch-enemy for most of the series. This is roughly the equivalent of an American officer during the Cold War being awarded Hero of the Soviet Union, First Class.
In The Road To Damascus, the sentient super-tank Sonny is repeatedly deployed against civilian protestors by the totalitarian government. Each time, they give him a medal, which only increases his self-loathing at being used this way. When he finally realizes that his allegiance is owed to the people rather than the government and turns against his corrupt masters, his first act is to shoot the medals off with one of his infinite repeaters.
In Tom Kratman's Caliphate, the Martinez Award is given by West Point to the cadet with the most demerits without having been kicked out. Cadet Hamilton himself doesn't consider it something to be proud of, but the Sergeant that he reports to after leaving schooling treats it as a genuine badge of honor, figuring that nobody who doesn't have what it takes could piss off so many people without having been kicked out of the Academy.
Several Harry Potter fanfics have him (and often others of his True Companions) awarded the Order of Merlin or the Special Award for Services to the School, only to turn it down since he doesn't want to be associated with previous holder(s) of the award (evil parent-betraying illegal rat animagus, murdering Dark Lord-in-training, and (depending on the fic) amoral, manipulative old headmaster).
Mello: You'll go down in the books, Matsuda. In the chapter called "Fucking Idiot Cowards of History", you'll be right at the top of the page. And L will be in second place after Liza Minnelli in the 'I Have Really Shit Taste in Men' awards.
The episode "Bombshells" saw B.J. being forced to leave a man behind. The Army decided to give him the Bronze Star for trying to save him, but B.J. was wracked with guilt.
BJ: The second I cut that rope I became a soldier.
Major Frank Burns was once awarded a Purple Heart for being wounded during a shelling. Of course the piece of shell they removed from him was from an egg. The medal was subsequently stolen and given to someone more deserving, a newborn baby who had been wounded before being born.
Another medal awarded to Burns was intercepted before he received it and given to an underage Marine Hawkeye decided not to allow to stay in harm's way after all.
In the 30 Rock episode "Rosemary's Baby", Liz was awarded a "Followship Award" (not a Fellowship Award) for effectively becoming a cog in the corporate machine.
After being forced to attend a sexual harassment seminar, she was given a certificate proclaiming that she was "no longer a workplace sex criminal," which she posted on her office door.
Lt. Shaw is the first person to start the massacre on the Scylla and is promoted to captain for it.
There's also Adama's medal in Hero, one of the second type. Slightly subverted since Roslin knows very well that he'll use it for self-flagellation, but the alternative is him quitting and she does genuinely want to honor him, sooo...
On Kings, David is the fifth person in Gilboan history to be awarded the Medal of Valor...not for his actions, but as an attempt to keep him quiet about other things. Even though he doesn't speak up on them, he refuses to wear the medal, and throws it away. This proves important...
Top Gear has the coveted Golden Cock award, a tiny rooster made from what is likely gold-painted plastic, given to, in their own words, "the presenter who's made the biggest mess of things in the past year."
Good Game's "Big Claim, Lame Game" award to a hyped-up but ultimately disappointing video game.
In a Peanuts comic, Lucy asked Schroeder, "What makes you think Beethoven was better than Elton John?" He promptly gave her a trophy for "most stupid question of the year".
One Dilbert comic has the Pointy-Haired Boss give an employee a t-shirt for his work on a project. Once the employee puts it on, it is revealed to say "Moron," with an arrow pointing up at the wearer's face. Then the PHB reveals that the employee's work was terrible and that he is fired.
In BattleTech the Draconis Combine has the 'Honor of Wakizashi'. It is awarded to a high ranking person who puts the honor of themselves or their family above the needs of the Combine. A person so 'honored' is expected to commit seppuku on receipt of the award.
The Battlefield series has the Purple Heart, achieved from a certain kill/death ratio depending on game (1:5 for 1942, 1:4 for 2, and 1:2 for 2142).
Spore has "Joker", which means that you cheated with the race that earned it, and you cannot get more Achievements with it (thus it overlaps with No Fair Cheating), "Pathological Cheater", for gaining 50 Joker badges, and "Dance With The Devil", which means you allied with the Grox and are thus a colossal Jerk Ass. There are also "Can't Win for Losing" (for dying in every stage of the game), and "General Custer" (for getting 30 followers killed and generally being The Neidermeyer).
Tactics Ogre: The Knight of Lodis has at least two unflattering medals with penalty effects: Bogus Hero, if you gain 20 or more levels while sparring your own units and Don Quixote if you attack someone and the counterattack damage deals 2/3 of your max health. Clerics and Priests can earn a third one, Gibe of the Fallen Angel, by killing three enemies with physical attacks.
It gets even worse in the sequels Portable Ops and Peace Walker, where it is all but stated/heavily implied that someone within the US government set her up from the start to be killed by Snake. At least the explanation in MGS3 had the justification that Volgin nuked the Sokolov Design Bureau and their being forced to have her killed to save face and get the legacy behind her being killed.
There are a number of Achievements on Xbox Live that mock you for having gained them. Usually they have zero points.
One that jumps to mind is Call Of Duty 4's achievement. If you fail to kill anyone in a multiplayer round, and die at least ten times, you get an achievement. Anyone looking knows that you either had a bad day, are obsessive compulsive, or suck.
This can be especially ironic if the achievement causes you to reach Sniper Milestone 3, that would reward you with the Razorback, a shield that keeps you from being backstabbed.
Guitar Hero 3 had ones for failing a song multiple times in a row, and failing at the 95% mark in a song.
The X360 version of Guitar Hero 2 gives you an achievement for your first failed song.
World of Warcraft: Wrath of the Lich King, jumping on the bandwagon, has at least one achievement that mocks the ones that have it: Obtain the Bloodsail Admiral's Hat... and try to get some fresh air every now and then.
Deaths By Hogger, enough said.
There's even a sort of inversion of the trope in the Leeroy Jenkins achievement, if you can pull off the infamous stunt that player attempted (provoking an entire room of baddies at once and killing them all). Notable in that the original Leeroy Jenkins died horribly and got his whole team killed with him in a hilarious manner, the actual achievement requires pulling the stunt off SUCCESSFULLY.
Having the achievement named after him might actually be a straight (if a bit complicated) version of this trope for the original Leeroy.
An achievement "Stood in the Fire"note the name of which is in and of itself, a reference to Too Dumb to Live behavior in boss encounters requires players to get killed by Deathwing. It's actually harder than it sounds, given how random Deathwing's attacks are.
Played even more straight now that Deathwing has become killable: You're awarded the achievement upon dying during either the Spine of Deathwing or Madness of Deathwing raid encounters. Not only does it retain its dubious value, but it now also signifies that it is likely the recipient's first time fighting Deathwing on that character.
The title "the Patient", earned after grouping with 50 random players with the Dungeon Finder tool on Heroic dungeons (roughly 13 or so runs, at minimum) tends to be seen as a mark of a relatively new maximum-level player who has not accomplished much in the way of raiding and has only been doing heroics so far.
City of Heroes awards badges for some rather dubious "achievements", including sustaining high amounts of damage, paying off debt (which is accrued each time you are "killed"), and time spent held in status effects.
At least most of the badges for such effects have cool names. Taking a lot of damage gets you the Tough, Indestructible and Unstoppable badges, which are at least okay.
These badges are less about making fun of the players, and more how awesome you are because you've died so many times, or taken so much damage. The final "Death" badge is Exalted.
Several of the bronze trophies in the PlayStation 3 version of Warhawk are awarded for such dubious feats as stepping on 5 land mines, or flying into your own aerial mine.
Silent Hill: Homecoming puts a rather bizarre twist on this. A document notes that Alex's father received a Good Conduct medal, a Purple Heart, and a Silver Star during his time in the Army. A puzzle shortly thereafter requires Alex to pin the medals on a uniform. However, the actual puzzle exists in the nightmarish "Otherworld," where the medals are Vile Conduct ("For atrocities committed") the Heart of Darkness ("For permitting others to suffer") and the Fallen Star ("For dereliction of duty.") The medals look like twisted versions of the real things, and the Vile Conduct metal even looks like Pyramid Head's helmet.
FreeSpace 2 has "Congratulations, you have attained the rank of Admiral. Now go read a book." This is because attaining Admiral requires completing the single-player campaign roughly a hundred times.
RollerCoaster Tycoon has some skull-and-crossbones awards for the "theme park with the lowest value", the "dirtiest theme park", "most dangerous theme park" (if you have too many roller coaster accidents). In fact, for all positive awards, a negative one existed.
Kingdom of Loathing has a number of these for the masochistic to collect and proudly display, such as 'Brave Sir Robin', for fleeing from 100 battles, and 'The Ghuol Cup' for eating 11 nasty undead dishes that permanently reduce your stats.
Arguably, the Cross of Glory in the light-sided ending for Knights of the Old Republic. Sure, you took out Malak, turned the Star Forge into slag, saved your crew ( You can still fail to save Bastila, though), and "broke the spirit of the Sith." Seeing as you caused the damn mess in the first place during your pre-amnesia tenure as Dark Lord of the Sith makes the honor somewhat dubious.
Warhammer Online has a series of titles unlocked by failure, including dying via mobs up to a million times ("The Tragic"), being killed up to 100,000 times by enemy players ("The Feckless") or falling to your death up to 5000 times ("The Pancake"). In addition to this there are specific titles for being killed by each enemy class, drowning in lava and several other dubious rewards that people nonetheless wear with pride.
Wing Commander has the "Golden Sun" medal, awarded for surviving the destruction of one's ship (by ejecting during battle). Each pilot is awarded it only once, and when you get it the first time your commander gives you a mild chewing out. After all, you generally get the medal after you failed at your primary objective.
Cybernations has the National War Memorial wonder, which can only be built if you've lost at least 50,000 soldiers in war. On the other hand, it's relatively cheap and provides a nice bump to national happiness.
The dreaded Fizbin of Misfortune, first introduced in Might And Magic 3, made appearances in the first two games of the Heroes of Might and Magic series. Just having it in your possession threw your general's morale and luck to the rock bottom, and the only way to get rid of it was to disband the hero currently carrying it. There was absolutely no upside to carrying this item around. However, if you were to dump it in the hands of an expendable rookie hero, who then suicidally attacked the strongest enemy hero...
In Need For Speed: Carbon, to unlock one of the parts you have to earn the consolation award. You get that for losing.
Another joke title, "Enabler", is acquired by completing a side-quest that involves bringing large amounts of booze to the town blacksmith.
There's even a title achieved for spending several real-time hours fishing on Valentine's Day — "Master Baiter".
Total War Shogun 2 includes an achievement for sinking or capturing a particularly powerful ship. Possibly due to a programming oversight, you still get this achievement if it's you that loses the ship in question.
Many games, particularly Shoot 'Em Ups, will award the player exactly 1 point for using a continue (sometimes also zeroing out the upper digits) up to a maximum of 9 times, while everything else is scored in multiples of 10. This makes the last digit of the player's score reveal how many times they continued.
Portal 2 gives an achievement for falling for GLaDOS's trap... and another for falling for Wheatley's.
Some achievements in The Sims Medieval aren't ones that are very good. A noteworthy one is "Have 25 people die in your Kingdom," which since the maximum population of hero Sims is only 12, 25 deaths have to come from either questing so badly you have to remake your heroes multiple times, or killing off a majority of your original NPC population, which weakens your kingdom.
Space Rangers has a few such medals, mostly given for cowardice or piracy.
In Tribes: Ascend one of the accolades that earn you points is "llama grab", gotten when you pick up a flag at a very low speed—which is likely to result in you dying before you get much anywhere with it and screwing up a faster moving teammate's grab attempt. While it still gives you points, it's less than even a standard flag grab and the description even says "not for use in any highlight reels".
Goldeneye: Source has a few in the form of achievements, including "004," which is awarded for blowing yourself up 25 times with your own mines, "Octopussy" for excessive camping, and "Who Throws A Shoe?" which is awarded to someone who plays as Oddjob-who has an insta-kill attack by way of his bowler-for essentially being the worst player in the round. Then there's the Awards, which are given every match, that point out similar things, and they're similarly both doled out for genuine skill-or a lack thereof.
Shooting the president in the Xbox 360 version of Secret Service earns you the zero-point achievement "The Exact Opposite of Your Job".
Lollipop Chainsaw has the trophy "Gunn Struck", which you get from being struck by lightning (or shocked by Vikke's electrical attacks) ten times.
Fate/stay night introduces one in the backstory: The Sealing Designation. It is a title of the "greatest honor" for magi who develop thaumuturgy that cannot be recreated as it is inherent to their body. The Mage's Association goes to great lengths to preserve this magic... by vivisecting the magus and preserving every part of their body for future study. Needless to say, the magus in question usually objects... because they won't be able to study it themselves.
Nerd: "I'll give [your copy of Nintendo World Championships] The Nerd Seal of Approval."
Pat: "So... what, you'll take a dump on it?"
Nerd: "No, that would be The Nerd Seal of Disapproval."
South Park had the school nurse given an award for her birth deformity, when she just wanted everyone to ignore it.
Not to mention Phony Psychic John Edward taking The Biggest Douche of the Universe award.
Randy also won a place in the Guinness World Records for The Biggest Piece of Shit Taken, to Sharon's disgust and shame. His competition is Bono, who turns out to be the Biggest Piece of Shit.
On The Simpsons, Homer went to his high school reunions and got all kinds of rewards that embarrassed Marge, like "Most Weight Gained" and "Least Distance Traveled to Get Here".
Homer, on the other hand, was proud to receive every single one and was outraged when they were confiscated on the basis of his failure to graduate.
Also when Homer disgraces the Stonecutters, he's forced to drag home the Stone of Shame while naked. Then when the Stonecutters discover his birthmark identifying him as the Chosen One: "Remove the Stone of Shame." "Woohoo!" "Attach the (significantly larger) Stone of Triumph!" "D'oh!"
Abe Simpson earned the Iron Cross - whilst serving in the US Army during World War 2, because of his incompetence at searching for mines.
On Futurama, Leela enters Nibbler in a dog show and wins... for Dumbest Pet in Show.
Also, Leela is elected to the Blernsball Hall of Fame... as "The Worst Blernsball Player Of All Time".
Now, now, she was an inspiration for female athletes everywhere... to not suck as bad as her, granted, but still.
On the Looney Tunes 1944 short "What's Cooking, Doc?" Bugs Bunny lobbies relentlessly for the Oscar, and gets a booby prize instead. He embraces it anyway.
Amusingly enough, Bugs (or rather, his producers) won a real Oscar in 1959, for Best Animated Short Film "Knighty Knight Bugs".
Ed Edd N Eddy, "The Good, The Bad, and the Ed": Eddy challenges Rolf to try and earn the Urban Rangers' toughest merit badge, the Hairy Chest of Resilience Badge. After losing by mere seconds, when Edd was convinced he had no chance at all against Rolf, Eddy was given... the Crybaby Boo-Hoo Badge. He's understandably incensed and, despite all but being in traction, demands a rematch.
One episode of My Little Pony: Friendship Is Magic had the Cutie Mark Crusaders performing a rock ballad in a school talent show, hoping they'll win an award and get their cutie marks. They do win an award... for comedy. Although the CMC was more disappointed that they didn't get their Cutie Marks. Subverted as the CMC were rather happy about their award, even thinking they should do more comedy.
Wing Commander Academy: a medal is refused by Blair after Tolwyn uses him as bait in a decoy operation. However, Tolwyn used the decoy operation because he was refused any reinforcements and had to use desperate measures.
The Darwin Awards, given to Too Dumb to Live people who improve mankind by "removing themselves from the gene pool" out of stupidity. Honorable Mention are given to those who survive the ordeal. One Honorable Mention recipient whose actions left him alive but unable to sire children actually submitted himself for the award, so he apparently didn't feel all that dishonored.
Halle Berry had the good grace to actually collect her award in person for Catwomanwith her Oscar statuette in tow. She even made a suitably effusive and weepy speech, as if she was winning the Oscar again; writer Michael Ferris also showed up to win his.
Bill Cosby had his Razzie made from marble and gold at the studio's expense when he "won" for Leonard Part 6.
Paul Verhoven also went to the ceremony for his Showgirls "honors" (and stated: "I got seven awards for being the worst, and it was more fun than reading the reviews").
Sandra Bullock handed out a free copy of the offending movie (All About Steve) to everyone in the audience. Then she won an Oscar the very next day (for The Blind Side).
When Brian Helgeland won a Screenwriting Oscar for his adaptation of LA Confidential, a reporter asked if he would accept the Worst Screenplay Razzie he "won" the day before (for The Postman). He said "Sure, why not?" and the Razzies founder went to Helgeland's office to give it to him. Reportedly he keeps them side by side on his shelf in his office as reminder of Hollywood's fickleness.
Tom Selleck requested delivery of his award for Christopher Columbus the Journey.
Some go there as a protest. J.D. Shapiro, one of the screenwriters of Battlefield Earth, received the Worst Screenplay statue at a radio show, and went to the actual ceremony to pick up the award for Worst Picture of the Decade, because he was fired from the movie in early production stages due to Executive Meddling.
J.D. Shapiro: Now, looking back at the movie with fresh eyes, I can't help but be strangely proud of it. Because out of all the sucky movies, mine is the suckiest.
Esquire magazine's annual Dubious Achievement Awards. The publishers' decision to discontinue the awards after 2008 was itself regarded as a dubious achievement by many of Esquire's readers.
The Ig Nobel awards are normally not this — they are given out to research that sounds silly, but is actually very useful (for example, new insights on structural failure gleaned from research into how a piece of dry spaghetti snaps). However, they are also sometimes given as a criticism, such as the Medicine award that was given to several tobacco company executives who testified under oath that they believed that nicotine was not addictive; the Mathematics award given to Enron, WorldCom et al "for adapting the mathematical concept of imaginary numbers for use in the business world"; and the Literature award given to the editors of Social Text due to their part in the infamous Sokal Affair. (Most winners who are actual researchers do, in fact, collect their awards at the annual ceremony. The Take That targets don't.)
Browse through the Guinness Book of World Records sometime. There are records in there that few people should want to have, such as "Most Facial Prosthetics" or "Largest Kidney Stone". Jonathan Lee Riches, who won the World Record for "most lawsuits" by filing hundreds of frivolous lawsuits from prison, sued the Guinness Book of World Records to the surprise of absolutely no one.
Dutch TV used to have a consumer show which gave a golden acorn award (noting that the Dutch word for acorn, eikel, also means "idiot" "dickhead") to companies that had particularly poor consumer service. In a subversion of the trope and owing something to the Dutch cultural mindset, these companies' CEOs would often appear in person to accept the award and promise a change for the better.
Another popular Dutch show, Kopspijkers, had an award that changed name every season, but was essentially given to the worst thing seen on TV. The evangelical broadcasting station that literally reduced an entire class of children to tears by trashing the gifts they bought for each other to give a rather convoluted message about not having sex before marriage was a memorable winner. So was the dubious but famous medium, who was displeased with the host and said that she was receiving the number 10 from the other side. Said host later left the left-wing public broadcasting station for a billionaire's pet project channel named Talpa, originally named Ten. His career never really recovered from that move. Huh, guess the other side is pretty vengeful.
The Purple Heart medal receive a mixed welcome from various members of the American military. Some see it as rewarding failure, while others see it as proof that you're willing to put your life on the line.
There have occasions of people getting military medals despite not having earned them. The objective is to avoid admitting a mistake was made or the military needs good publicity. This often overlaps with Bling of War in communist nation-states.
In communist and single-party nation-states the Bling of War often overlaps with Medal of Dishonor. While every society can fall victim to political awards, non-democratic nations are more likely to give medals and orders that promote loyalty to the state. Compare the amount and type of military and civilian medals between nations here: .
Members of the US Army's Officer Candidate School elect one candidate "most expendable".
Each graduating class at West Point "awards" its lowest-ranked cadet the dubious honor of being "the goat." Additionally, each cadet (usually around 1000 or so) in the class donates a dollar to the goat, so at least he or she gets something out of it.
The Lowsman trophy, a statuette of a player fumbling a football, is awarded annually to the last player selected in the NFL draft. The player is also awarded the title "Mr. Irrelevant".
Former U.S. Senator Bob Kerrey (Democrat of Nebraska) wasn't proud of his Medal of Honor (awarded for a routine SEAL action for essentially political reasons) and Bronze Star (supposedly for wiping out a VC base; actually a village of civilians including children).
Gamespot devotes a whole section for this in their year-end awards, "Dubious Honors", where all but one award ("Best Game No One Played") are bad achievements. Awards vary, but every year included "Most Despicable Use of In-Game Advertising", "Most Disappointing Game", "Worst Game Everyone Played", and "Flat-Out Worst Game".
Likewise, X-Play has The Golden Mullet Awards for the worst games of the year. The award is named after the first game to receive a 1 out of 5, Aquaman: Battle for Atlantis.
They also hosted a segment recognizing games they couldn't give a full review on because the producers refused to allow a 0 out of 5.
Interesting, even the biggest awards in a field can become this. There are certain awards from the big award shows that some people are a little suspicious of because of a track record that they might be cursed. A couple:
Best New Artist at the Grammys: The award is notorious for its completely erratic track record. You either go to soaring new heights or you completely disappear from the public eye. Almost every Best New Artist winner is asked afterward if they're worried about the curse. More specifically, the 1990 award, which was awarded to Milli Vanilli and was later revoked. They had planned to give the award to one of the other nominees (Neneh Cherry, the Indigo Girls, Soul II Soul, or Tone Lōc), but none of them wanted it.
Best Supporting Actor and Actress at the Oscars: Louis Gossett Jr. said, after his win, that he felt it was something of a double edged sword. While he did have an Oscar to his credit, he said he felt like he was trapped in a strange gray area where smaller productions don't think they can afford you (since you're an Oscar Winner) and big productions don't think you can carry a film on your own (since you're a Supporting Actor.) They also have a similar hit and miss record as Best New Artist, with winners such as Brenda Fricker and Mercedes Ruehl virtually disappearing afterwards.
Most "Car of the Year" awards are similarly erratic. The Simca 1308 beat out the first BMW 3-series for the 1976 European COTY, for instance.
Peter The Great really loved medals of this type. In 1709, he "awarded" (in absentia) an "Order of Judas" to Ukrainian hetman Ivan Mazepa for betraying him and siding with Swedish king Charles XII. In 1714, he introduced the Drunk Medal◊, a huge chunk of cast iron (weighing between 9 and 18 pounds), to be worn for a week as a punishment for being a Vodka Drunkenski.
When Finland ended up fighting alongside Nazi Germany to recover territory lost to the Soviet Union during the Winter War, their ranks included Jewish officers. Some of them received the Iron Cross, one of Nazi Germany's highest awards, which they all told the Nazis where to stick.
The Bad Sex Prize, awarded annually by Literary Review to the writer who has produced the worst sex scene in literature that year.
SF fandom has (or had) the Hogu Awards, a parody of the Hugo Awards with such categories as Worst Fanzine Title, Best New Feud, Most Desired Gafication (or in non-fanspeak, the person the voters would most like to leave fandom - in a bonus parody of the Trans-Atlantic Fan Fund that sends British fans to the US and vice versa, the winner of this award is said to be eligible for the Mid-Atlantic Fan Fund) and Special Devo Award for Harm to Science Fiction. The Hugo is a statuette of a space rocket on a wooden plinth; the Hogu is a wooden plinth with a scorchmark on top.
The Golden Poo from the consumerist. Normally reserved for the Bank of America, Electronic Arts got the dubious honor (along with the hit in stock).
"Most Improved" awards at school are often treated with embarrassment by students, since they imply that you weren't very good to begin with.
Italian football has Bidone d'oro, the golden trashcan, which is given to the "worst" player in Serie A. This award has only been given to top club players, so it's really closer to biggest disappointment. France also has Ballon de Plomb, the lead ball, for the most disappointing player in Ligue 1.