What's essential in his oeuvre?
Like most dbag hipsters, I think Nebraska is his best album. And even though it's dark it has an amazing set of songs and their all really cool and listenable. Johnny Cash could've covered it in its entirety. It's just Bruce's home demos that he did for an E-Street album, but then put out the demos instead.
Born to Run is a classic. Every song is pretty great and the production is amazing. It's Bruce at his Springsteeniest.
The first two albums stand alone and are very different from the rest of his work. Greetings From Asbury Park is (was) intended as a singer-songwriter album, and it's heavily Dylan influenced in its mad rush of language and imagery. That's where you get great songs like "Spirit in the Night" and "Blinded by the Light" (both of which were covered for hits by Manfred Mann). Bowie actually covered "It's Hard to Be A Saint in the City." (It didn't come out until the Ryko reissues.)
The Wild the Innocent and the E-Street Shuffle might actually be my favorite Springsteen album. It was an earlier version of the E-Street band with a jazzier drummer and a jazzier pianist and consequently it's got a looser, jazzier groove. "Rosalita" is the semi-hit from that album, and it's still a total rock and roll blast of exuberence.
Darkness on the Edge of Town was my high school album. It is a fairly dark, angsty and serious album but has an incredible collection of songs. "Candy's Room" is one of my favorite rockers by Bruce.
I don't love The River, even though it was rapturously received at the time. Too many depressing songs about the effects of Reaganomics.
Born in the USA was his biggest hit, but the only song I want to listen to from that era is the B-side "Pink Cadillac" (a hit for the Pointer Sisters). I don't like the 80s production on that album. Too many punted dumpster drums.
There are some good things in his later work. Probably Tunnel of Love is the best - it's about the breakup of his first marriage.