He was once the voice of a young generation, but nowadays Richard Linklater is a lot harder to define. Going through his oeuvre can be a somewhat bewildering experience, especially when picking the wrong films (or picking them in the wrong order). That's not to say his oeuvre houses a random collection of styles and genres. Linklater does keep to a somewhat limited set of approaches, it's just that each one is wildly different from the next. It makes him an interesting director to explore, but it also increases the chance you might run into some stinkers along the way.
Linklater started out in the 80s, but very few have seen It's Impossible to Learn to Plow by Reading Books, his very first feature film. People only started to notice Linklater when he directed Slacker and Dazed and Confused, two films that focused on young kids growing up, doing very little of anything at all. Dazed and Confused in particular grew out to become a real cult favorite, though I can't say I found much to like there. The clichés and stereotypes are so thoroughly American that it became impossible for me to relate to Linklater's 70s nostalgia.
In '95 Linklater started the Before trilogy, probably his most broadly appreciated set of films to date. Ethan Hawke and Julie Delpy take on the parts of two fated lovers, with each film running through different key moments in their relationship. While very dialogue-heavy, there's a certain lifelikeness and spontaneity to the films that makes them quite irresistible. The first two films (Before Sunrise - 1995 - and Before Sunset - 2004) are more romantic in nature, the last one (Before Midnight - 2013) is a bit more dramatic. Watching them in order of appearance is recommended, though not absolutely required.
I lost track of Linklater during the late '90s, but early on in the '00s he gave his career a surprising twist. Waking Life is a daring experiment that delivers 100 minutes of philosophical meanderings in animated form. Linklater made use of early rotoscoping techniques to transform live action footage into animation, effectively turning the whole film into a painfully long trip into uncanny valley. It didn't really help that the philosophical topics were quite weak and were never explored in any meaningful way. Linklater would revisit this setup five years later. A Scanner Darkly would add some more explicit scifi elements (and Keanu Reaves), which ended up only making things worse. A Scanner Darkly is by far the worst film he ever made.
But Linklater also tried his hand at some more commercial projects. School of Rock is a Jack Black comedy aimed at a younger audience, Bad News Bears a sport flicks with a post-Bad Santa Billy Bob Thornton looking to repeat his success and Bernie is another Jack Black comedy, though with a slightly darker edge to it. These film are quite variable in quality, but it's clear that Linklater fares better when he can do more personal projects.
In 2014 Linklater put himself back on the map with Boyhood, a project he worked on intermittently for 12 years. The idea was to follow a family, with the actors aging in real time. While the setup is intriguing and the execution was clearly geared at providing a grand dramatic experience, the mediocre drama and overly long running time stood in the way of Boyhood becoming a great film. I found it rather lifeless and overdone, which is a shame as the idea did appeal to me. The film was received extremely well though, so your mileage may vary.
Linklater's career isn't finished yet. Just last year he directed Everybody Wants Some!!, a more "modern" version of his early films, this time harking back to the 80s. Not quite as successful, but Linklater's entire career is characterized by ups and downs. I'm not the biggest fan, but I do keep an eye on him and I do try to watch his films whenever I get the chance. If you're looking to break into his oeuvre, the Before trilogy is probably the best place to start. If you're a bit more seasoned, films like Boyhood and Walking Life might be more to your liking, but there's just no guarantees with Linklater.
Best film: Before Sunset (4.0*)
Worst film: A Scanner Darkly (1.0*)
Average rating: 2.35 (out of 5)