Here are five quintessential single guys. The movies listed here each tell different stories in different ways but they all touch on one or more of the following common single guy themes: meeting women, understanding and relating to women, falling for a woman, or getting over a woman.
The Top Five Single Guy Movies
5. Chasing Amy, 1997, is not a perfect film but it deftly and humorously showcases the crucial issue men often face in new relationships when they encounter difficulties accepting and getting over their new partner's past. The story, loosely, follows the budding relationship between comic book artist Holden McNeil (Ben Affleck) and Alyssa Jones (Joey Lauren Adams). Director and writer Kevin Smith complicates the prelude to the relationship by casting Alyssa as a lesbian (or bisexual, depending on your interpretation of the material), and setting up a somewhat forced buildup in which Holden falls in love with her and tries to convince her to be with him. That Alyssa accedes only casts further doubt on her initial characterization.
However, once Holden and Alyssa get together, the film becomes compelling and very true-to-life. This is most apparent when Holden hears rumors about Alyssa's past from his longtime friend and roommate Banky (Jason Lee) and subsequently struggles to come to grips with the information. Eventually, he confronts Alyssa about her past - in another scene that could be familiar to many guys. Ultimately, this is what makes Chasing Amy memorable - the effect of the past on new relationships - and why it is a worthwhile single guy film.
4. The Brothers McMullen, 1995, is one of those surprise single guy movies disguised as a traditional drama. In fact, the film is very much about how men struggle to deal with relationships and love.
The plot follows three Irish Catholic brothers on Long Island -- each of whom confronts in his own way problems with relationships and women. Jack (Jack Mulcahy), the oldest, find himself straying from a comfortable marriage into an affair; Barry/Finbar (Edward Burns), the cynic who doesn't believe in love, is forced to confront his fears of commitment when he finally meets a woman for whom he cares deeply; and Patrick (Mike McGlone), the youngest, weighs the consequences of maintaining a familiar but less-than-perfect college relationship or making a clean break and moving on with his life.
The Brothers McMullen is effective as a guy movie because it captures different questions and issues about women and relationships different men might face at different times in their lives. We may not experience all three episodes portrayed in the film, but there's a good chance we've faced at least one of them.
3. The Tao of Steve, 2000, is about Dex (Donal Logue), an overweight and exasperating (but endearing) slacker who manipulates the philosophies of Lao-tzu, Heidegger and Groucho Marx into a foolproof theory of dating --The Tao of Steve -- which provides a system of rules and guidelines for transforming ordinary guys into charismatic Steve McQueens.
The Tao of Steve is great for its truth in showing how deliberate actions and signals can affect success or failure with new women. Dex, with his Tao of Steve rules, knows how to "eliminate desire" in front of a woman, how to "be excellent" in front of her, and, most of all, how and when to pull away and feign a lack of interest - all of which, of course, are geared to make the woman more interested.
The film succeeds merely for showcasing the extent to which men can redefine dating as a theory and game, but it takes it one step further when it pits Dex's elaborate system against a situation for which he has no rule: a woman he loves.
2. High Fidelity, 2000, based on the best-selling novel by Nick Hornby, focuses on Rob (John Cusack), a thirtysomething music store owner and pop music junkie just out of a long relationship, who uses music to define and measure all aspects of his life. Despite the pop music backdrop, High Fidelity is every guy's story, a film that hits many of the unspoken truths and defining feelings men have about women and relationships. High Fidelity is perhaps most effective in how it captures the disorientation and actions following the end of a relationship: how Rob reorganizes his record collection in an effort to find security in the familiar; how he reassesses his past relationships and contacts old girlfriends; how he fumbles in his efforts to win back his ex-girlfriend, Laura (Iben Hjejle); how he tortures himself with thoughts of Laura and her new lover; and how ultimately he gets it right when he has an opportunity to reconcile with Laura.
1. Swingers, 1996, is perhaps the single-best all-time guy movie, and certainly the top single guy movie. Set in Los Angeles, Swingers follows the lead character Mike (Jon Favreau), a comedian trying to make it in LA after having moved to the city from NY, as he struggles to get over a six-year relationship that recently ended and move on with his life. The movie's brilliance is in how it hits so close to come. Every guy who's ever tried to get over someone special has been Mike once and the movie captures those moments extremely well: how Mike has trouble talking to new women without comparing them to his ex, how he focuses on the past by looking at old snapshots, how he fumbles an opportunity with a new woman, and how he has trouble talking to his friends about anything but his ex.
Fortunately, Mike's friends remain determined to prop him up and get him back on his feet. From the ultra-slick player Trent (Vince Vaughn), who shows Mike how to be "money" and talk smoothly with women, to Sue (Patrick Van Horn), who speaks bluntly at times but does it for the best of reasons, to Rob (Ron Livinsgton), who engages Mike in honest and open conversations, Mike's friends all are there for him, each in his own way. Ultimately, these friendships, as well as Mike's introspection and growth throughout the movie, allow him at the end of the film to do what was inconceivable as the movie began: move on.
Frank Gullo
February, 2002