Looking at Deadpool's bibliography and trying to find a place to start can be intimidating for new readers, but luckily Deadpool himself has some helpful recommendations for his own favorite comics starring himself. While the Merc with a Mouth might not be the most unbiased judge, his trademark self-awareness makes him uniquely suited to figuring out which of his comic appearances are the best.
One of the toughest challenges for comic readers is trying to figure out which issues to start off with to get to know a new character, especially when that character has a history as rich as Deadpool. Over the course of 30 years, the mercenary has found himself appearing in countless series, miniseries, limited series, and one-shots. And that's just when he's appearing in the comics of other characters. His own stories in which he stars is a whole other wide collection in itself.
In Wolverine #20 by Benjamin Percy and Adam Kubert, Deadpool takes a detour into a local comic book shop to relive his glory days. Deadpool fondly looks at and admires a bundle of comics, exclaiming, "I used to be awesome, man!" This bundle of comics includes New Mutants #98, Deadpool #1, and Uncanny X-Force #1. All three are the perfect back issues for fans looking to understand the character through his most essential tales.
New Mutants #98 by Rob Liefeld and Fabian Nicieza is where Deadpool makes his first-ever comic book appearance. In it, Cable has a bounty on his head and the Merc with a Mouth is the man trying to collect. Released in 1991, Deadpool is still years away from the zany character he'd become in due time, with his quippy wit reaching more of a bitter snark than the fourth wall-breaking whimsy he'd be known for. If anything, there may be a smidge more emphasis on Deadpool's lethal nature as a hitman than on his quips during his initial appearance. Still, it's a significant issue that plants the seeds for what Deadpool would become.
After a few recurring appearances and starring in a number of miniseries, Deadpool was finally given his own ongoing self-titled series in 1997. Deadpool #1 by Joe Kelly and Ed McGuinness is what establishes the definitive voice of the title character. He's more wacky and funny than intimidating now, but Kelly doesn't forget to add in moments of actual drama to offer the character some development throughout the series. For the first issue, though, the comedy is emphasized to let readers know what kind of tone they were in for from the start. And perhaps it's worth noting the first page of the issue sees Deadpool call someone an, "ignorant simp," decades before the word "simp" would become popularized.
Finally, there's 2010's Uncanny X-Force #1 by Rick Remender and Jerome Opeña. In this series, Deadpool isn't so much the lead star as he is a co-star when Wolverine assembles his own team of mutants, Deadpool included. Deadpool sets the story in motion during the first issue when he ventures into the Temple of Apocalypse where he is ambushed by War, the Final Horseman, moments after seeing the Clan Akkaba enforcing a disturbing sacrifice ritual. What makes this series so essential is that this one brings Deadpool back to his original roots, putting emphasis on action and drama, with mild humor. Deadpool's sarcastic wisecracks remain, but he treats each mission with sincerity and the utmost urgency, retaining the lethal danger factor that has intrigued and entertained fans (and Deadpool himself) since 1991.