Sasuke Uchiha was a major character in the Naruto universe, second only to its title protagonist. The story followed his bond with the young Uzumaki, an inevitable descent into darkness, and after hundreds of episodes, a gradual path toward redemption.
With a massive history and one of the most detailed backstories in the anime's universe, Sasuke's endeavors have resulted in many heartbreaks that have evolved his Sharingan and shaped the person that he is. By analyzing the worst that ever happened to him, we might better appreciate the decisions he made -- as erroneous as some were.
10 Embarrassed By Rock Lee
During Team Seven's first encounter with Rock Lee, the taijutsu master completely embarrassed Sasuke and might have even rendered him unable to participate in the exams were it not a fortunate intervention.
This was in spite of the fact that Lee had no ninjutsu or genjutsu to speak of, dominating the intrepid young Uchiha through the merits of his hard work alone. It was a massive blow to his ego and one which shocked Sakura and Naruto in equal measure.
9 Given The Curse Mark
Having learned of Sasuke's potential and intrigued by his now rare bloodline, Orochimaru ambushed Team Seven in the Forest of Death, leaving his curse mark on his target.
This would be against the ninja's will, even if it would exponentially increase his power at the cost of his soul. Immediately after realizing what had happened, Kakashi warned him of what the brand could portend. Though Sasuke would heed the warning at the time, it would later be disregarded as his thirst for power grew more insatiable and he became desperate to bring his brother to justice.
8 Dominated By Gaara
Since their first match in the Chunin Exams had not been properly concluded, Sasuke was eager to defeat Gaara as the Jinchuriki rampaged across the forest. Unfortunately for him, he was defeated with relative ease, the chidori at his disposal insufficient in overcoming the sand monstrosity.
More mortifyingly still was Naruto's subsequent victory against the same opponent. It proved that Uzumaki's strength had progressed far more than his own, coaxing him toward more desperate measures in order to remain unrivaled among Konoha's ninja and so that he might properly enact his revenge.
7 Hunted By His Former Friends
After Sasuke had turned on Konoha, even those who had attempted to retrieve him (including Kiba, Neji, Shikamaru, and even the usually forgiving Choji) had all admitted he was a danger to others and must be put down. Given the gravity of the crimes he had already committed at that point, their anger against him was warranted.
The only person to disagree was Naruto Uzumaki, convinced that if he is unable to bring his friend back to the light, he would make for an unsuitable Hokage. Ultimately, his ability to redeem Sasuke was only for the fact that he could challenge his burgeoning strength.
6 Beaten To A Pulp By The Sound Four
Impatient for his new host's body, Orochimaru expedited Sasuke's decision to join him by sending his lieutenants to beat him up. They would not forcibly abduct the ninja, however -- their combined success against him was only to demonstrate his lacking strength.
Providentially, the fallen Sannin's tactic would be a success, with their battle serving as the final catalyst for him to join them. He was enamored by their power and the mastery they possessed over their bequeathed might.
5 Lost His Encounter Against Itachi
When Sasuke realized that Itachi was in Konoha (and hunting Naruto, no less), he leaped at the chance for vengeance. Though the ninja arrived in time to challenge his Akatsuki adversary, the fight was depressingly lopsided, proving that his power had not grown much since the harrowing night of the Uchiha genocide.
He was completely incapable to stop his older brother or save his friend, forced to rely instead on Jiraiya's strength in lieu of his own. This was a profound demonstration of Sasuke's impotency, compelling him to pursue darker alternatives to the path he had been on.
4 The Uchiha Genocide
As a young child, Sasuke was forced to watch as his brother sliced down his kinfolk and parents, unable to do anything to prevent it. His efforts to stop Itachi were met with a fist to the gut, crumpling him so that his physical pain might dully resemble his emotional agony.
His older brother had taken everything from him, forcing the newly made orphan to live as an anomaly in Konoha as the subject of suspicion and curiosity. It would also render him an appealing target for Orochimaru's future plans.
3 Becoming An International Fugitive
When Sasuke had obstructed the Five Kage summit and fought the Raikage directly, it was primarily so that he could reach Danzo Shimura and force him to answer for his crimes. Nonetheless, it rendered him a national fugitive across all nations, encouraging a hunt far more expansive and vigorous than merely his former friends.
Regardless, few were able to challenge his strength by that point, and he had embraced the notion of living as a feared force for evil. So long as they respected the power at his disposal, their ire was inconsequential.
2 Losing His Arm
The final fight between Sasuke and Naruto was one that would devastate the arena, leaving permanent reminders to battle for each combatant. Preparing a final strike to finish off their foe, both of their arms were completely destroyed in the process, resulting in a draw.
Even if Naruto would decide upon having his replaced through Hashirama cells (much like how Obito mended his own body), his limb would retain an ivory pallor that reminded him of their fateful battle. Sasuke would not replace his arm as a sign of atonement for the egregious sins he had committed.
1 Wrongfully Killing His Brother
Since his introduction, Sasuke's singular objective was to kill Itachi Uchiha and avenge his clan. After heartache and struggle, he was able to accomplish exactly that. Their legendary battle would be witnessed only by Zetsu, one which darkened the sky and shook the earth.
Though his victory may have satisfied him at the time, Sasuke would later discover that Itachi had only agreed to the genocide in his brother's best interest. It was on the order of Danzo Shimura, with his sibling obliging his sinister will under the condition that Sasuke would be spared from his wrath.