As a songwriter, it's only natural that I'd be interested how other songwriters keep fresh and subvert chord forms and lyrical ideas. It's the same for authors - how one keeps from cliched writing, or how to make a worn idea feel new, etc. In the case of songwriters - at least, bad songwriters - it's, ahem, a slippery slope. There are only so many chords and, especially in rock'n'roll or the blues, a songwriter can find him or herself stuck in a corner with all-too-familiar chord changes. Lyrically, songwriters are closer to poets (though, holding up even a Paul Simon lyric sheet pales in comparison to John Ashbery or Louise Gluck) and it's much too simple to write couplets of cliched rhyme. It's no secret that having the ability to know when something is well-worn, be it chord changes or lyrical content, is what separates the interesting songwriters from the boring ones.
We're all aware that John Lennon, Paul McCartney, Patti Smith, Bob Dylan, Carol King, and Nick Cave are widely considered some of the best songwriters in music history. Yet, because their style has been imitated and commercialized and crammed down our throats since childhood, it's also easy to find a lot of what they'd written as hackneyed and cliche: such are the pitfalls of fame and glory.
When I sit down to write a song I make a choice. I decide if I want the song to go a more traditional route and, if yes, I work out ways to subvert it just slightly, to make it fresh at least to myself. Sometimes it's as simple as making the V chord minor; or instead of changing from I to vi to IV to V, I may try I to bVI to iv (flatting the typical minor vi chord andmaking the usual major IV chord in the scale minor) to V. Of course, it also depends on the mood of the song; sometimes, there is nothing wrong with traditional. If I decide to go another route, perhaps more experimentally, I will usually try to ground the song in some way, either with motifs or by using a traditional structure with chord forms (and sometimes lyrical content) that have nothing traditional about it. (I don't really consider myself all that experimental when it comes to songwriting anyway, but it has been remarked my songs contain a certain "quirk" to them, whatever that means; the farthest out I've gone was a song called "Horse Face in the Flames" that was based around a tritone pattern. Even so, crowd reaction to this song live was intense: you either loved it or really, really, really hated it. Goes to show how sensitive our ears are to music without formal chord structures and melody, even though serialism has been part of our musical language for well over fifty years.)
I also like to listen to songwriters I find that subert these traditional structures. Part of what makes songwriting so much - and likewise, writing stories - is finding ways of saying what's already been said before in different, fresh ways. Here are some songwriters who, I believe, have been on the cutting edge but, for whatever reasons, haven't hit the mainstream. It's probably a good thing - unlike the Beatles or Bob Dylan, their music hasn't been widely imitated and, as such, they remain nuggets of inspiration.
(Projects: Wolf Parade, Sunset Rubdown, Moonface)
I have yet to find a fault in Spencer Krug's songwriting. Everything he does is exciting and blasting with emotion. Yet, it's also surreal and timeless, carnivalesque and epic.
Matthew and Eleanor Friedberger
(Projects: Fiery Furnaces, solo work)
Like Krug above, the Friedbergers have a flare for the epic. Their lyrics are more "literary" (in fact, I've also considered the sibling duo to be the leaders of "lit rock," screw off Colin Meloy.) They're not afraid to take chances either (see: Rehearsing My Choir). But their strength really lies in making a hodge-podge of styles a cohesive whole.
(Projects: The Fresh & Onlys, solo work)
Recently, Tim Cohen has become quite prolific in the indie world, releasing at least one record a year over the last 3 years. Each one builds on the last. He's famous for his lo-fi garage rock band, The Fresh & Onlys, but his solo record, The Two Sides of Tim Cohen, shows a more subdued, atmospheric approach to songwriting.
(Projects: solo work)
Lekman is a crooner with a keen eye for detail. He has an almost note-perfect pop sensibility. His use of samples in songs is wonderfully integrated with the song itself it's almost unnoticeable.
(Projects: solo work, sometimes known as Kurt Vile and the Violators)
Vile is the workingman's songwriter. There is a grit and dirt in a songs, so much so that even when he's singing a light melody or a lullaby, there is a wariness and weariness that unhinges the song and releases it into the ether.
Garbus most certainly on the experimental side of songwriting. She subverts and reinvents where a song should and will go every time. Because she isn't afraid to be in-your-face about it and to twist a song into unexpected places, sometimes it takes a couple listens to get used to it. But once you do (and if you can), the rewards of her music pay off in big ways. She's a great lyricist too.
Honorable Mentions: Bill Callahan, Joanna Newsom, Alec Ounsworth, PJ Harvey, and Cass McCombs.