My guess is, the most enticing thing to a modern audience about Where the Day Takes You will probably be the chance to see an ensemble of famous actors in the up-and-coming stages of their careers. Dermot Mulroney, Sean Astin, Lara Flynn Boyle and Balthazar Getty lead the charge, with Kyle MacLachlan, Alyssa Milano, David Arquette, Ricki Lake and future mega-star Will Smith in supporting roles and Christian Slater and Adam Baldwin making brief appearances. Most of them play a group of loners and drifters in the Los Angeles area, led by King (Mulroney), who is just finishing up a three-month prison stint. They wander around town, begging for money, trying to entertain themselves and avoid authority while each dealing with their own personal problems and addictions.
The DVD cover for Where the Day Takes You has a couple of quotes claiming the film's gritty reality is shocking, but I think only adults shielding themselves to the way things are would be taken aback by any of the movie's content. I realize the movie's nearing its 20th anniversary, and I'm part of the everything's-accessible internet generation, but I'm rarely shocked by even the most extreme cinematic sights. I'm 23 now, maybe once I hit 30, my idea of the way things are will be set, and every cultural shift from then on will rile my delicate sensibilities. Until then, my problem with films like these is that there's always at least one character, usually the protagonist or a sidekick, who's just a little too smug when it comes to their revelations about "life". Where the Day Takes You employs an "interview" device where an unseen person (Laura San Giacomo) talks to King about his daily experiences, and the film dances on that line between wise and holier-than-thou know-it-all, just barely landing in the right camp thanks to Mulroney's generally optimistic attitude.
These kinds of films are also generally trapped between a rock and a hard place when it comes to the plot. Personally, I like movies that are more about atmosphere and the company of the characters (like Stranger Than Paradise, for example), but those kinds of films are rarely made. Thus, we have to have some sort of plot, and the writers have to choose whether to lean towards a "happy" ending that runs the risk of sugarcoating the environment they've painstakingly recreated or go with the traditional, problematic "dark" ending, which usually ends up mired in melodramatics and predictability. Having explained them, I can't really say which one Where the Day Takes You goes for, lest I spoil the movie, but a short patch during the middle to end of the second act where the movie looks like it's going in a different direction is much more interesting; ultimately, the movie doesn't bring anything I felt was new to the table.
Of that ensemble cast, the strengths really start at the top and go on down, but Sean Astin stands out as Greg, a meth addict whose addictions are threatening to break him. Ultimately, the character's arc during the third act wasn't as good as I was hoping, but Astin's twitchy, needy user act never devolves into caricature and you really feel for the character. Peter Dobson (looking and sounding like Craig Bierko) plays a villain named Tommy Ray that has a standing beef with King. The performance is good, but it's never really clear exactly what the issue between the two characters is; more emphasis on the rivalry could have helped to drive the plot.
In the end, there isn't anything wrong with Where the Day Takes You, it just didn't grab me the way it might have grabbed someone else. Like my CD, at some point, the film stopped being a film and became more of a time capsule, a captured moment where a piece of art was saying the same thing as some viewers were thinking. If you're not one of those people, then maybe this isn't the film for you, but to those who were, I may not agree, but I know how you feel.
The Video and Audio
Dolby Digital 2.0 Stereo is unremarkable. It doesn't sound crisp, but it sounds clean enough, with clear dialogue and music. It's not a directional soundscape, but it's closer to the "reasonably adequate" level of quality I'd expect from a 90's catalog release. English subtitles are included.