First...flashback to Deadpool's adventures in yesteryear with Iron Man!
Then...Deadpool is hired by a demon to reclaim damned souls!
Plus...Wade gets in touch with his feminine side!
At the Daily Bugle, Peter Parker is being ignored once again despite saying some incredibly shocking things. J. Jonah Jameson is bent on getting some scandalous story about a binge-drinking Tony Stark/Iron Man. Jameson kicks Peter out of the meeting to get pictures of Spider-Man. Peter leaves and sees Flash Thompson park his car in a handicap parking spot. Peter tries to tell Flash his folly but Deadpool interrupts and steals Flash's car.
Deadpool nearly runs over some kids (the Power Pack) and then meets a man named Mr. Vetis. He hops in the stolen car with Deadpool and makes a business proposal. Mr. Vetis and his employers would like Tony Stark to continue drinking and they want Deadpool to ensure that Iron Man begins drinking again. Mr. Vetis asks Deadpool to name his price. When Deadpool is assured his own laser disc factory he is eager to sign the contract. Mr. Vetis then explains that he is a demon and he hopes to store some of the power he is smuggling from Hell in Tony Stark's body so that his boss doesn't notice the power he is hoarding.
Ignoring the moral implications of helping a lowly demon hide power from Hell in a human's body, Deadpool visits a liquor store to get booze to entice Tony Stark. He finds a thug standing over the store clerk. Deadpool offers to party with the thug. The thug lowers his defenses and Deadpool kills him. Deadpool then takes a lot of alcohol in a Santa-like sack.
Deadpool next visits Stark Industries to search for clues as to Tony's whereabouts. He finds Tony at a run-down hotel. Tony is a mess (and watching the old "Howard the Duck" movie) and Deadpool knows just how to help him feel better. The men grab a tall bottle of booze and start dumping it all. Tony loves how empowered he feels by not drinking. A news story springs onto the television about a nuclear power plant that is near melting over. Tony wants to spring into action but Deadpool knocks him out. Deadpool then puts on the Iron Man armor, explaining to a lifeless Tony that this job requires the kind of Iron Man that Tony can't be anymore: a drunken one. Deadpool flies away while swigging copious amounts of alcohol.
On his way to the nuclear power plant, Deadpool sees a robbery. He almost goes to help but then remembers that his is flying over Hollywood and figures it is just a movie. It isn't. He arrives at the power plant and learns that the nuclear rods need to cool off. He tosses the rods into the ocean.
Mr. Vetis arrives and confronts Deadpool about their contract. Deadpool is adamant that the contract merely said that Iron Man had to drink. Deadpool, dressed as Iron Man, technically did just that. Mephisto appears and confronts Vetis about his practice in hiding Hell's power on Earth. Mephisto sucks Vetis into Hell. Deadpool turns around to see Cable. The two teleport away to stop a vile plot of Mr. Sinister's Mexican brother Señor Sinister.