Wade Wilson aka Kingpin. While they are best known as villains, Thanos and Kingpin will do anything for love, with Thanos literally killing half of the universe and Kingpin choosing to be with his partner even when it isn’t optimal for his survival. However, Deadpool has been involved with both love interests of Thanos and Kingpin, which has put the antihero in hot water in more ways than one.
Thanos’ famous love interest is Mistress Death, whom fans were made aware of in explosive fashion in the Marvel Comics series Infinity Gauntlet by Jim Starlin and George Perez. While Thanos proves his love to Death by using the Infinity Gems to extinguish half of all life in the universe in her name, Death never returns his affection. That isn’t to say Mistress Death is incapable of love, however, as she falls head over heels for Deadpool and Thanos takes extreme measures to ensure the two never see each other again. In Thanos vs. Deadpool by Tim Seeley and Elmo Bondoc, Thanos makes it so Deadpool is permanently immortal so he can never be with Mistress Death. He also beats him to a bloody, unkillable pulp out of extreme jealousy.
Before Deadpool’s romantic connection with Mistress Death came to a head with Thanos, the Merc with a Mouth moved in on Kingpin’s wife years before the two were married. In Daredevil: Deadpool Annual ‘97 by Joe Kelly and Bernard Chang, Deadpool and Daredevil forces to take down Typhoid Mary until Deadpool betrays Daredevil to hook up with their target. In current Marvel Comics, Kingpin and Typhoid Mary are married, so while Deadpool’s romantic relationship with Typhoid Mary doesn’t put him in Kingpin’s crosshairs like with Thanos, he pays for it in a different way. When Deadpool falls in with Typhoid Mary, she uses him to betray his partner then dumps him the second she is free.
Deadpool pays dearly for both romantic involvements that make him the rivals of Thanos and Kingpin in different ways. While the dalliance with Kingpin’s future wife doesn’t involve Kingpin directly, Deadpool gets involved with a villain that will eventually fall in love with someone as despicable as the Kingpin and quickly learns his lesson. Deadpool’s relationship with Mistress Death has more violent repercussions as Thanos is directly involved there, showing Deadpool the danger of messing with the Mad Titan.
Based on his comic history, it is clear that Deadpool is much more promiscuous than he is portrayed in film, where he is dedicated to one woman even after her death as shown in Deadpool 2. While on his sexual walkabout throughout his comic book career, Deadpool came across two love interests that he paid for pursuing and in the process put himself on the radars of both Thanos and Kingpin in a bad way.
