4. Bob, Agent of HYDRA (Marvel Comics)

As much as I like Deadpool, my favorite part of his stories has always been his supporting cast. Whether we’re talking Bind Al, Weasel, the Ghost of Ben Franklin, or whoever, I have a soft spot for them. But there is one Deadpool Sidekick who stands out above the rest: Bob Agent of HYDRA.

HYDRA sucks at recruitment and training, so it was inevitable that one of their agents would betray them and go rogue. It was also inevitable that agent would be a quivering coward. And that’s what Bob is. In fairness, he was literally trained to be cannon fodder. HYDRA training even dictates that if you hear the sound of Wolverine’s claws popping, you run like hell. Bob is the kind of poor sap who would try to be a pirate and wind up with scurvy. And yes, that literally happened. Poor Bob.

As you would expect, being Deadpool’s sidekick is not the safest of jobs and Bob’s track record proves that. The guy has been shot, stabbed, and had both his legs broken and still he is ever willing to team back up with Deadpool. Bob is Deadpool’s Harley Quinn, but only in the “psychologically unhealthy relationship” sense.