I enjoy this quirky movie quite a bit, and get more out of it with each subsequent viewing. Okay, so it's got Vince Vaughn playing yet another semi-obnoxious lothario. It's got a displaced New Yorker who is -- SURPRISE! -- neurotic and whiny, something we've only ever seen in almost every single Woody Allen film (amongst others). It's got the Token Cool African-American Friend Who Doesn't Have That Many Lines. Yet at the same time, this was actually Vince's FIRST semi-obnoxious lothario role (which no doubt set him up for being cast in further such roles), and his character does redeem himself by being sincerely concerned about his friends, going above and beyond the call of duty to help them. The Neurotic Displaced New Yorker actually grows as a person with the help of his friends, and becomes balanced and likeable. And the Token Cool African-American Friend STAYS cool throughout the film without any over-the-top comedic cracking of the veneer during stressful moments.
The music is excellent, especially if you're into Swing, Big Band, and Jazz. I think it was the music (and the attendant anachronistic zoot suits) that caught my fancy on the first time through, and the plot and characters kinda grew on me in subsequent viewings. The excessive use of pseudo-hipster slang either enchants you or grates on your nerves; it's not a take-it-or-leave-it part of the film. Personally, if I hear anyone using "money" as an adjective ever again, my first response will be physical violence. And that's the ONLY reason I haven't given this film full marks. But it IS a fairly big reason for me.
Still, this is one of those films where the popularity and fan base started out slow and small but grew to cult status with exponential speed. Like most cult films, it's realistic(ish) and a Thought-Provoking and Irreverent Commentary on Aspects of Modern Society, but it's nowhere near as "gritty" as most cult films. In other words, it's in colour, it doesn't have a depressing ending, and there are no supremely wise taxi drivers dispensing zen-like wisdom. Also, not a lot really happens in the film, but it plays so much like the better kind of fly-on-the-wall Reality TV show that it's easy to get sucked into the (admittedly thin and rambling but engaging) plot. It's got loads of homages to other popular films, TV shows, and whatnot. It's very well-written, very well-acted by all involved, it looks really good, and (apart from hearing "money" and/or "baby" every 20 seconds) it sounds really, REALLY good. "Swingers" is one of those small, independent films which far outclasses most of the big-budget blockbusters, and launched a LOT of promising and successful careers. The behind-the-scenes documentaries are good for watching through ONCE, to get the stories behind the making of the film, but are so full of self-congratulatory back-slapping and gag-reflex-inducing mutual appreciation that you probably won't want to watch them ever again. The "Swing Blade" short film included in the bonus features, however, I could watch again and again and again until my eyeballs shrivel; it's hilarious!
However much fans of this movie rave about it (and I count myself as one of those), "Swingers" admittedly isn't going to be to everyone's taste. I would recommend renting it first to see if it's your kind of film, and if it is, THEN buy it. It's an exceptionally good kick-back-and-relax film to watch while downing a few cocktails, either alone or with your friends.