The Straw Hat Pirates are an eclectic group that has terrorized the seas and entertained fans for more than 20 years. And while its band is famous for its powerful members, not all of them are heroically infallible. One resident of the Thousand Funny has in fact been remembered by fans and even referred to in the industry as the Straw Hats' weakest member.
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That person is none other than the Sniper King and God, Usopp. Usopp is the cowardly trickster of the Straw Hat pirates whose sniping skills perfectly compliment his need to be as far away from his opponents as possible. Though he isn't exactly known for his muscle, Usopp is one of the most active fighters in the series. This list will be going over some of the brightest victories in Usopp's adventure (& some of his most humiliating defeats).
10 Defeats: Kuro
Usopp's introduction in the series didn't start off on the right foot. He made it abundantly apparent that he would be the comic relief coward of the group and didn't show off the proper muscle to prove otherwise. His main shining moment was finally telling the truth about a pirate raid for the first time in years, but it would sadly fall on deaf ears.
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This would actually force the poser adventurer to actually stand up for his village and to disastrous results. He'd go on to challenge the traitor of the island and the leader of the Black Cat Pirates, Kuro, and easily fell to theguy's obviously superior strength. He would then go on to require Zoro's help to take down Jango.
9 Victories: Chew
Usopp more than proved that he could be a jolly companion to the Straw Hat Pirates, but it took him quite a while to actually prove his strength. That wouldn't be until Arlong Park in which Usopp would get a glimmering and rare instance of stoic heroism. After learning about Nami's plight, Usopp helped fight against the Arlong Pirates and personally went up against Chew, a fishman who spat water like a pistol.
While a lot of the encounter involved Usopp running away (a literal running gag across the series), he'd eventually turn back and use a variety of his best tricks to get his first victory in the story.
8 Defeats: Franky Family
This one is perhaps Usopp's most humiliating defeat to date. When the Straw Hats decided to get the Going Merry some repairs, he was in charge of one of the briefcases carrying the Straw Hats' newfound treasure. However, he wasn't expecting the city of engineers to also have a few hoodlums and fell prey to an early villain of the beloved arc, the Franky Family.
Usopp didn't stand a chance and was mugged and left bloodied in the middle of the street. Not only did he lose a good portion of the Straw Hats' money, but he came to realize just how weak he really was as a pirate.
7 Victories:Daddy Masterson
Though this one isn't canon, it's one of the most beloved filler stories in the anime and perhaps the most defining story for Usopp's sniping skills. When a cool pair of goggles caught his eyes, Usopp found himself competing for it and his safety against the Marine sniper turned bounty hunter, Daddy Masterson, aka Daddy the Father.
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Masterson once challenged Usopp's father, Yassop, to a shoot out and inevitably lost, deciding to end his Marine career right then and there. He'd go on to challenge Yassop's son to a similar contest and would unfortunately lose in a similar manner (and to a slingshot no less). Usopp doesn't get that many opportunities to hype up his sniping skills, so the anime really gave fans a gift with this one.
6 Defeats:Sugar And Trebol
During the Dressrosa Arc, Usopp was part of the Straw Hat team that was left behind to fight the Donquixote Family. He would get the unlikely job of getting the save the island in its entirety when he challenged one of Doflamingo's commanders, Trebol, and the person transforming people into submissive toys, Sugar.
Unfortunately, his first go about it didn't go as planned. He was beat down by Trebol's clearly superior strength and was force fed his own, spiced grape. In turn, the pain from the grape would contort his face so much that he'd end up scaring Sugar to exhaustion. While Usopp was clearly defeated in this encounter, he did get to accomplish his mission and saved Dressrosa's citizens from Sugar's curse.
5 Victories: Sugar
While his initial bout with Sugar was ambiguous in its outcome, their second clash wouldn't have as vague of a winner. Sugar would eventually shake off her daze and immediately went after Luffy and Law. If she could manage to make everyone forget about the leaders of the revolution, the battle would be a clear victory for the Donquixote Family.
However, Usopp immediately caught eye of her from across the kingdom. To be able to shoot her from miles away, Usopp was able to unlock his Observation Haki to see further and more accurately than his old scope ever could. This time around, he didn't have to be poisoned to win.
4 Defeats:Douglas Bullet
In another non-canon bout, Usopp got to challenge to one of Gol D. Roger's most infamous crew members. Douglas Bullet was once a demented beast that wasused as a child soldier but would eventually be defeated and taken in by Roger. After Roger's execution, Bullet would go on a rampage that required an entire Buster Call to quell.
In One Piece: Stampede, this man conspired to take down both the Marines and the new generation of pirates with his bare hands and made Usopp one of his targets. While Usopp made a brave effort and even got to plant a few traps along the way, he'd once again prove just how human he really is.
3 Victories: Miss Merry Christmas And Mr. 4
The Alabasta Arc and the clash with Baroque Works was perhaps the Straw Hat Pirates first encounter with a big name organization. While Luffy was off challenging the big kahuna, Sir Crocodile, Usopp and newfound crew member, Tony Tony Chopper, went up against one of the organization's most infamous bounty hunting pairs, Miss Merry Christmas and Mr. 4.
Merry Christmas would trap her opponents with her Mole Mole Fruit by grabbing them from underground and dragging them to Mr. 4 whose monstrous strength would bash them with his four ton bat. Usopp's wits had to match Chopper's beastly power to be able to defeat a genuinely powerful and unique duo.
2 Defeats: Monkey D. Luffy
This is one of the saddest encounters in the series. As stated above, Usopp's defeat at the hands of the Franky Family inspired new feelings of inadequacy that only the meanest of viewers had thought of before. When he learned that Luffy wanted to trade away the Going Merry, he felt as if he himself was being abandoned and quit the crew.
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In a last ditch effort to save the Going Merry, Usopp challenged Luffy to fight for it. While his efforts were well-considered and well fought, even Usopp knew that he couldn't win this fight.
1 Victories: Perona
In what may very well be Usopp's most well fought battle to date, he went up against an opponent that literally only he could fight. Perona was the Ghost Princess of the Thriller Bark Pirates who used her Hollow Hollow Fruit to remove all of the positive energy within ambitious opponents.
This made her a nightmare for fighters like the Monster Trio but near powerless against Usopp, a guy who gave up on the fight as soon as it started. Having learned that he was immune to Perona's powers (not that this was a good thing), Usopp would go on to use his sniping skills and best trickery to take her down.
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