For a brooding loner who prefers to work alone, Batman sure does team-up with other superheroes a lot. Aside from cultivating an extensive network of heroes in his Bat-Family, the Dark Knight is a member of the Justice League and the Outsiders and has teamed up with multiple heroes from other universes on many occasions.

Although team-ups between heroes is commonplace in comics, a hero/villain team-up is somewhat rare, especially when the rogues' gallery is as dastardly as Batman’s. But it has happened, so here are 10 Times Batman Teamed Up With His Greatest Villains.

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10 Lex Luthor

10. Lex Luthor - Panel from Kingdom Come

Though not a primary antagonist for Bruce Wayne, Lex Luthor and Batman have come into direct conflict before, usually through Justice League business and extensively during No Man’s Land, when Luthor tried to buy most of an earthquake-ravaged Gotham City. However, politics makes strange bedfellows, and in Kingdom Come, the Dark Knight and Luthor form an uneasy alliance to stem the influence of meta-humans on world affairs.

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Although reveling in the newfound partnership, even remarking that “had I known that a common enemy could bring us together, I’d have invented one years ago,” Luthor was eventually betrayed by Batman, who in typical fashion, only agreed to a partnership to discern Luthor’s plans.

9 Poison Ivy

Before her recent death, Poison Ivy was one of Batman’s more prominent enemies, obsessed with saving all plant life from destruction at the hands of man. To that end, her use of plant-based chemical pheromones to control men and twist them to her whims has put Batman under her thrall many times in the past.

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A notable exception to this occurred in Batman: Arkham Knight. Teaming up out of necessity rather than mind-control, Poison Ivy and Batman joined forces to defeat the Scarecrow, following the detonation of his fear gas over Gotham City by the Cloudburst device. Achieving a mutual respect, the video game team-up ended for Ivy in much the same way as it did her comic book counterpart: death.

8 The Penguin

Although an easily recognizable member of the Dark Knight’s rogues gallery, the Penguin has never been a physically or psychologically imposing figure. In the run-up to Tom King’s City of Bane, it is revealed that a woman by the name of Penny Cobblepot (presumably the Penguin’s wife) has been brutally murdered by Bane’s forces.

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This prompted Cobblepot to reveal to Batman Bane’s coercion of Arkham Asylum, which he has used as a staging ground to take over Gotham from within. Hoping for vengeance by proxy, the Penguin’s team-up with Batman was short-lived, as his hide-out in the Batcave was compromised by Thomas Wayne, the Flashpoint Batman.

7 Mr. Freeze

Perhaps the most tragic of all Batman’s villains is Victor Fries, whose sub-zero condition was caused by an accident in cryogenics while searching for a cure for his terminally ill wife. Most modern iterations of the character see the motivations for his crimes as funding his research into reanimating his beloved Nora.

He recently got his wish fulfilled in Detective Comics #1015. Also suffering from the same cryogenic condition that Victor is, Nora joins her husband in a crime spree to fund their retirement. However, Nora soon tires of Victor’s overbearing nature and leaves him. In a desperate attempt to win back his wife, Victor approaches Batman for help, which the Dark Knight accepts in order to stop Nora’s crime spree. With so much animosity between these two adversaries, this team-up is bound to remain on thin ice.

6 Ra's and Talia Al Ghul

Ra's and Talia al Ghul

One team-up with a villain happened in Batman’s first encounter with him! Having deduced Batman’s identity as Bruce Wayne, Ra’s Al Ghul approached him in the Batcave to enlist his help in finding his kidnapped daughter, Talia. As Robin has similarly been captured, Batman agreed to the partnership, but later revealed Ra’s culpability in the abductions all along.

The whole episode was a test of Batman’s worthiness to succeed Ra’s as his heir, by marrying Talia. In truth, it’s Talia and Bruce’s partnership here that bore more fruit, as through their mutual affection, Damian Wayne, the current Robin, was born.

5 Bane

Batman and Bane fight back-to-back

The last thing anyone would want to do with someone who broke their spine would be team-up with them, but Bruce Wayne has done so with Bane on at least two occasions. In Batman: Vengeance of Bane II, he and Bane briefly collaborated to take down a cadre of Venom pushers and users, with the Dark Knight promising to take down Bane when they were done.

Further, in No Man’s Land, Batman convinces Bane to break his deal with Lex Luthor, as he had been acting as his enforcer in an earthquake-ravaged Gotham. However, despite their occasional partnerships, Bane and Batman remain mortal enemies, of which the recent City of Bane arc can attest.

4 Two-Face

Another of Batman’s villains who began his relationship with the Caped Crusader as an ally was Gotham’s District Attorney, Harvey Dent. But Dent’s pre-Two-Face partnership with the Batman was not the only one they enjoyed. In Hush, the facially reconstructed Dent saved Batman from the titular villain by shooting him off a bridge and into a river.

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Further, in Face the Face, the Dark Knight actually trains a reformed Harvey Dent to take his place in the year absence he took following the events of Infinite Crisis. Despite their antagonism, Batman and Two-Face seem to be able to work together at times, harkening back to the early beginnings of their relationship.

3 Catwoman

Batman and Catwoman have a long and storied history, a good half of which is spent either being at odds or romantically linked. Their most notable modern-age team-ups have been the widely popular early 2000s tale Hush, wherein exploring their budding romantic relationship, Catwoman aided Batman in his struggles with his rogues' gallery and a Poison Ivy-controlled Superman.

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During the more recent Tom King run on Batman, Bruce and Selina very nearly tied the knot, and although Selina backed out to allow Batman to keep his crime-fighting edge, it’s only a matter of time before these two team-up again, romantically or not.

2 The Joker

With a history of violent antagonism as virulent as that between Batman and the Joker, a team-up is the last thing any fan would expect. However, these bitter arch-rivals have managed to bury the hatchet on a few occasions.

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The most recent was during the Dark Knights: Metal crossover, which prominently featured a Dark Multiverse version of Bruce Wayne who had succumbed to the Joker’s toxin. Named The Batman Who Laughs, Batman was so desperate to defeat this deadly new adversary, he enlisted The Joker to help him. The team-up proved successful, as they were able to defeat The Batman Who Laughs and keep him from destroying reality.

1 Joe Chill

Joe Chill and Batman, Batman Year 2

Batman: Year Two chronicled the Dark Knight’s struggle with Gotham’s first vigilante, The Reaper, whose bloody rampage set Batman, the GCPD and Gotham’s underworld against him. In order to put an end to The Reaper’s rampage, Batman agrees to an uneasy alliance with the mob, who assigns him a partner.

That man happens to be Joe Chill, the man who killed Bruce Wayne’s parents. The personal struggle Bruce feels here is palpable: on the one hand, he wishes to murder Chill to avenge his parents and on the other hand, he wants to honor his vow to them to rid Gotham of crime without stooping to the same level as criminals (or The Reaper, for that matter). With a surprising conclusion to the dilemma, this team-up is definitely the most difficult the Batman ever had to participate in.

NEXT: 5 Marvel Heroes Batman Would Team Up With (& 5 He Would Hate)