Over the course of two decades, One Piece has introduced fans to hundreds of characters, but the story's main focus has always been on the Straw Hats crew. Usopp was the crew's third member, and he serves as the Straw Hats' marksman, but he is also a competent tactician and engineer. For the most part, Usopp is a coward, but when push comes to shove, he can be a brave fighter who is willing to sacrifice himself for his friends.
Naruto was One Piece's biggest competitor for over a decade, and the series gave fans a world filled with shinobi who can perform powerful jutsu by manipulating and releasing chakra. If Usopp were to ever find himself in the Naruto universe, he might be able to beat a few of these shinobi, but there are other ninja that he would definitely not stand a chance against.
10 Can Beat: Shino's Insects Would Be Useless Against Usopp
Shino is one of the smartest members of the Konoha 11, and he possesses a unique jutsu that makes him a formidable shinobi. As a member of the Aburame Clan, Shino's body is host to several insect species, and he can use these insects to drain an opponent's chakra or paralyze them.
Usopp doesn't use chakra, so the insects would be completely useless in that regard. Shino could use his insects to create diversions, or he can try to paralyze Usopp, but Usopp can stop the bugs by simply hitting them with some kind of fire.
9 No Chance: Usopp Would Never Get Past Gaara's Sand
Gaara started off as a villain, but he has since become one of Naruto's closest friends. The 5th Kazekage was once Shukaku's jinchūriki, and as a result, he is capable of manipulating sand for offensive and defensive purposes.
None of Usopp's explosives would be able to stop Gaara's sand, and when it finally catches him, Gaara can use it to crush Usopp's entire body. Usopp could try fighting Gaara from afar, but ranged attacks are completely useless against Gaara since his sand shield instinctively protects him from danger.
8 Can Beat: Karin May Be An Uzumaki, But She's Not A Fighter
Karin may have grown up in the Hidden Grass Village, but she is a member of the Uzumaki Clan. Like other members of her clan, Karin possesses a powerful life-force that grants her significantly higher chakra reserves and vitality. She is also capable of healing people who bite her, and she can use an incomplete version of her clan's Adamantine Sealing Chains technique in battle.
Unfortunately, Karin is not much of a fighter, so there is a good chance Usopp's Pop Greens will be enough to defeat her. She might be a sensory ninja, but Usopp doesn't use chakra, so he could snipe her from afar without being noticed.
7 No Chance: Minato Is Just Too Fast
Many consider Minato to be the fastest shinobi in history, but he was also incredibly smart and skilled, which is why he was eventually named the 4th Hokage. Minato sacrificed himself to save the Leaf Village from the Nine-Tails, and in the anime, he managed to wipe out an entire army of Stone ninja singlehandedly during the 3rd Great Ninja War.
Usopp may be a good shot, but he would never be able to hit Minato with any of his ranged attacks. A Melee battle would be disastrous for Usopp too because Minato can just end the fight with a single kunai or Rasengan.
6 Can Beat: Usopp Stands A Chance Against Deidara Because Of His Haki
The Akatsuki is a group of powerful rogue ninja, and several of its members have fairly tragic backstories. Deidara hailed from the Hidden Stone Village, and thanks to his rare chakra nature, he was recruited by the Akatsuki to become the organization's explosives expert.
Deidara can mold explosive clay with mouths in his palms and chest, and he then launches his creations at opponents before detonating them. Under normal circumstances, someone like Usopp would be a goner, but Usopp possesses Observation Haki. This Haki allows Usoop to sense another person's intent and location, so he can hit Deidara with his Pop Greens while the Akatsuki molds his clay.
5 No Chance: All Of Usopp's Attacks Would Just Pass Through Obito
It was fairly obvious that Obito was Madara all along, but he still did a good job of fooling the entire ninja world. As an Uchiha, Obito possesses the Sharingan, an ocular jutsu that allows him to read his enemy's movements. This is especially useful against enemies who use ranged attacks since it gives someone like Obito more time to react and evade.
If that wasn't problematic enough, Obito's Mangekyo Sharingan allows him to use a space-time ninjutsu to transfer himself and other objects into another dimension. This ability would cause all of Usopp's attacks to simply pass through Obito's body, and he can then teleport behind Usopp to finish him off.
4 Can Beat: Usopp Can Destroy All Of Sai's Drawings
There are certainly shinobi who can beat Sai, but he can also defeat quite a few ninja thanks to his ANBU training. Sai happens to be a skilled artist, and he incorporated this skill into his fighting style. He specializes in the Super Beast Imitating Drawing technique, which allows him to use his chakra to animate any ink drawings he creates.
These drawings can be formidable, but they are still made out of ink, and Usopp can destroy them by simply throwing water on them. With enough force, these drawings will pop like balloons, so Usopp can get rid of them if he shoots them in the right spot.
3 No Chance: Hidan's Immortality Is Too Problematic
Of all the Akatsuki, Hidan is by far the most sadistic member, and that is because he loves killing people to satisfy his God, Jashin. In doing so, Hidan learned a forbidden jutsu which turns him into a human voodoo doll.
All Hidan needs is a sample of his opponent's blood, and when that happens he just needs to form a symbol on the ground, and while he's inside that symbol, any damage his body sustains is shared with his opponent. Unfortunately, this jutsu also gave Hidan immortality, so even if Usopp avoids his scythe, he would never be able to take Hidan down.
2 Can Beat: Tenten Has Ninja Tools, But Usopp's Aim Is Much Better
Most of the Konoha 11 have saved the day in some way, but Tenten has never really been put in such a situation. Tenten was in a team with Neji and Rock Lee, both of whom were strong and capable shinobi, and although she is skilled in her own right, she is nowhere near as strong as them.
Tenten is a weapons specialist, and she is known for overwhelming opponents with ninja tool barrages. Usopp can theoretically avoid most of her kunai, shuriken, and other weapons with his Observation Haki. She may be a ranged fighter, but Tenten's aim is abysmal when compared to Ussop's, and she doesn't really have any defensive ninja tools that can block his attacks.
1 No Chance: Usopp Is No Match For Itachi's Sharingan
Itachi Uchiha impacted the series in a variety of ways, and the argument can be made that he is the strongest shinobi that his clan has ever produced. Itachi mastered the Sharingan at a young age, and as a result, he would be able to dodge all of Usopp's attacks effortlessly.
Like Obito, Itachi unlocked the Mangekyo Sharingan, and with it, he can trap Usopp inside a genjutsu that could leave him comatose. Itachi can also summon black flames that can burn Usopp and all of his Pop Greens until nothing is left. If that wasn't enough, Itachi can use his Susanoo's shield to block all of Usopp's attacks, and he can then use the sword to instantly defeat him.