Given his illustrious career as one of the galaxy's greatest smugglers, Han Solo has made quite a long list of enemies. With a gun in every space port, Solo was sure to run into a crime boss, a bounty hunter, or a Sith lord who wanted him dead (or at the very least frozen in carbonite). Without his resourcefulness, quick wit, and adaptable co-pilot Chewie, every encounter with a foe could have been his last.
A fast draw with a blaster and possessed of some helpful skills courtesy of a stint in the Imperial Navy, Solo managed to outmaneuver every sticky situation he encountered, from escaping Death Star detention levels to destroying Starkiller Base. Nevertheless, for every Rodian with an itchy trigger finger, there was an even more dangerous threat lurking in the shadows.
10 Greedo
One of Solo's most well-known enemies, if his most innocuous, Greedo was a Rodian who jumped at the chance to gun the smuggler down. When Jabba the Hutt put out the bounty on Solo's head, Greedo thought it would be the perfect opportunity to make him pay for an old grudge.
In "The Luckless Rodian", included in the anthology From a Certain Point of View, Greedo was revealed to have fallen deeply in love with Uncelta, a woman he "cherished" beyond measure. When she left him for Solo, he became fixated on revenge, and just foolhardy enough to try to outdraw him in the Mos Eisley cantina.
9 Tasu Leech
The leader of the criminal organization Kanjiklub, Tasu Leech was a brutal brawler who gained notoriety for speaking with his "Huttsplitter" rifle rather than using Galactic Basic, a language he considered to be for "soft people" like Han Solo. Together with his lieutenant Razoo Qin-Fee and Crokind Shand, they made their credits running exotic contraband and weaponry to high bidders.
Having grown up on the Hutt-controlled world of Nar Kanji where humans had to fight to survive, he was forged in a crucible of pain and suffering, and doesn't take excuses for smugglers who fail to deliver their goods. Luckily for Han and Chewie, a few escaped Rathtars made short work of him and the other members of Kanjiklub.
8 IG-88
Known as one of the bounty hunters recruited by Darth Vader to track Solo in The Empire Strikes Back, IG-88 was an assassin as legendary as Boba Fett. His origin is included in "The Long Game", a one-shot story from the pages of Star Wars: Age of Rebellion Special #1, and paints the picture of a truly merciless killer every bit as frightening as the Terminator.
Having killed his creators, the droid reprogrammed himself into an indefatigable killing machine, and with the ability to weaponize and customize any part of his body with "the obsession of an artist", he did not desire the same compensation as most organic beings, and therefore collected bounties for the sheer thrill of it.
7 Dryden Vos
Outwardly urbane but no less ruthless in his private ventures, Dryden Vos was the public figurehead in charge of Crimson Dawn, one of the galaxy's most powerful crime syndicates while the Empire was in its infancy. He had hundreds of smugglers, bounty hunters, and thieves on his discreet payroll, all the while hobnobbing with the galaxy's social elite.
When Solo went behind his back on their coaxium deal, he earned a powerful enemy. Since the only way out of Crimson Dawn was death, Solo sealed his fate turning the coaxium over to Enfys Nest.
6 Jabba The Hutt
Running afoul of Jabba the Hutt was career suicide for a smuggler, and no sooner had Han and Chewie dropped their cargo of spice than they received a 50,000-credit bounty on both of their heads. Apparently, being boarded by a Star Destroyer was enough for Solo to risk not only his reputation, but his life.
Unfortunately for Solo, Jabba didn't forget about his unpaid debt, and even after he helped the Rebel Alliance secure countless victories over the Empire, he still wound up a prisoner in his palace. Jabba's influence stretched far beyond Tatooine, and he could afford to recruit bounty hunters like Boba Fett to bring Solo in frozen in carbonite.
5 Boba Fett
One of the most notorious bounty hunters in the galaxy, Boba Fett earned his legacy by repeatedly bringing in high bounties and getting out of impossibly risky situations alive. He tracked Han Solo to Cloud City on Darth Vader's orders and was able to later bring him to Jabba the Hutt, collecting on two bounties for his trouble.
Presumed dead following Solo's escape from Jabba's Palace, he survived being eaten by the Sarlacc, and lived ascetically until being reunited with his Mandalorian armor. After joining Din Djarin in his intergalactic adventures, Fett built on his reputation as a prestigious mercenary by returning to Jabba's Palace and taking over the Hutt's seat of criminal power.
4 Grand Admiral Thrawn
The most famous villain in the Expanded Universe, Grand Admiral Thrawn was taken from Star Wars Legends and canonized in Star Wars: Rebels, where he continued to be one of the most dangerous leaders of the Imperial Remnant. A brilliant strategist and ruthless tactician, Han Solo, Leia Organa, and Luke Skywalker were all in his crosshairs at one point or another.
With what remained of the Imperial Fleet, he chased Solo and his compatriots to the edges of the galaxy, using many of Solo's greatest skills against him. Had it not been for greater enemies (like the Yuuzhan Vong), and Thrawn being forced to work together with the New Republic, he might have succeeded in killing Solo.
3 Darth Vader
The Dark Lord of the Sith didn't soon forget the cocky pilot who sent him spiraling away from the Death Star just as it was about to explode. Though the act inadvertently saved Vader's life, it put Solo on a shortlist of people the Sith lord needed removed from his path to Luke Skywalker.
For Han Solo, Vader was a powerful foe, and not just because he could rip his blaster from his hand with the Force, or inflict torture on him. With the might of the Empire behind him, Vader orchestrated a deal with Lando Calrissian to have Solo frozen in carbonite and promptly delivered to Jabba the Hutt, proving that for all Solo's bravado, any interaction with Vader would be both deadly and humbling.
2 Kylo Ren
Supreme Leader Snoke's personal enforcer and the leader of the Knights of Ren, Kylo Ren was a formidable warrior known for his mercurial mood swings and his unique dark side abilities. Born Ben Solo, he was Han Solo's only son, and a former apprentice to Luke Skywalker until his fall from the light.
Though he presented a considerable threat to the Resistance with the military might of the First Order at his back, his danger to Solo was far greater and more personal. The smuggler couldn't help but drop his guard around him, and Ren took advantage of his stubborn belief that he could reach whatever part of his son was still redeemable. Solo underestimated Ren's duplicitous nature and the power of the dark side, and paid for it with his life.
1 Emperor Palpatine
Solo's vendetta against the Emperor has a long history, going back to his tumultuous years as a cadet in the Imperial Navy. After enlisting as a means to leave his sordid life on Corellia behind him, he was sent to the most inhospitable worlds to suppress local incursions. The Empire used and abused its troops, but that was nothing compared to what it did to alien species it encountered, like the enslaved Wookiees.
In one form or another, Solo fought against the Emperor and all he represented for most of his life as part of the Rebel Alliance, and even in his later years as part of the Resistance against the First Order. But he could never have predicted that it was Palpatine, by way of Supreme Leader Snoke, who could turn Ben Solo to the dark side, and get his only child to kill him.
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