The Scott Pilgrim series, written and drawn by Bryan Lee O'Malley, isn't the most philosophical or complex or beautifully drawn comic I've read since getting back into these things, but I can't think of one that I've enjoyed more. Four volumes of a planned six have been released so far (they come out roughly once a year), and I'm on my second reading of the set.
Scott, our protagonist, is a 23-year-old living in Toronto and trying his hardest to keep his life as uncomplicated as possible. As the first book (Scott Pilgrim's Precious Little Life) begins, he's dating a 17-year-old high-schooler named Knives Chau - the age difference does not go unnoticed by Scott's friends - but he soon becomes obsessed with Ramona Flowers, a rollerblading Amazon.ca delivery girl who doesn't exactly dig on Scott...at first. After some awkward interactions and metaphysical run-ins, Scott finds out that if he wants to date Ramona, he must defeat her seven evil ex-boyfriends in combat. That pretty much sets up the series, and we're tossed into Scott's world of indie rock, video games, and the growing threat of emotional maturity.
Although the series is based in real-world Toronto, its reality owes owes a lot to video games and comic books. Fights end with a puff of smoke and a loot drop, neighborhood bars have glowing save points in the corner, and rock bands have the ability to knock an entire audience unconscious. That's mighty difficult to pull off without seeming goofy or pandering, but O'Malley keeps his story grounded emotionally, allowing room for some of the more bizarre and broadly comic moments. In fact, there's a distinct melancholy that hovers over the books. It's never heavy-handed, and it isn't always immediately noticeable, but it gives the characters a kind of depth that catches you off-guard. For all his faults, you still can't help rooting for Scott: he's kind of thoughtless, but he's (generally) sweet and (mostly) sincere.
I can't think of any reason to not recommend this series, although I think some basic pop-culture literacy helps if you want to get the most out of it. But even if you don't catch that a chapter title was snagged from a New Pornographers song, or that fictional bands Sex Bob-omb and The Clash At Demonhead are old NES game references (Super Mario Bros. 3 and Clash at Demonhead, respectively), you'll find plenty more to love about these books. There are dozens of great little moments and lines that I could blabber on about, but I'd rather let you find them on your own.