Deadpool started his vocation in the Special Forces. After leaving the SF, he began a storied career as a mercenary for shady and unsavory types, such as Cobra. As his career grew, he started taking jobs for the good guys. He came to the attention of G.I.Joe when they had a particularly complicated operation where they needed complete plausible deniability. Hawk commented on how he was the near opposite of Snake Eyes. Where Snake Eyes was a silent warrior, Deadpool was a "Merc with a mouth."
Deadpool, the world's preeminent Merc With A Mouth, is known the world over. Not only for his success rate but for his mouth running non-stop. He is one of few people who can say they fought Snake Eyes to a standstill. He was planning on killing him and could have, but he decided to keep him around because in his words, "He balances me out and is an incredible listener. I really think he gets me."
When he's not cashing those sweet sweet checks from Uncle Sam for the stuff he does when the Joes can't, Deadpool, the Merc with a mouth is a Great Lakes Avengers...
The GLA is a disaster waiting to happen. Between Deadpool's over-the-top destructive antics and the GLA's absurd power set it's a wonder Milwaukee still exists. Nevertheless, they have had limited successes, whether despite, or in spite of Deadpool's membership on the roster is up for question.
The Merc with a Mouth has odd tastes when it comes to his vacation destinations. One such spot is the Arctic Circle where he was "Searching for that bastich Santa". Awoken one night by the sounds of hoofs on the roof of his cabin he ran out in his PJs.
Deadpool is known for killing stuff, blowing stuff up, and talking to no one in particular during battle. He also happens to be absurdly open-minded about different beings. When he met Sqweeks, he jumped at the chance to ride a scooter and be friends with a transforming robot. Sqweeks, in turn was happy to be friends with the foul-mouthed murder machine. Of course, the fact that Sqweeks made his arm a massive weapon of destruction had little to do with Deadpool's decision. Deadpool convinced Sqweeks to change its paint to be more "on brand," and the two have been inseparable since.