Almost twenty years after Harry Nilsson's death, a boxed set of 17 discs' worth of his recordings, The RCA Albums Collection, came out last week, coinciding with Alyn Shipton's biography Nilsson: The Life of a Singer-Songwriter. Nilsson has never fit comfortably into pop music's history. His biggest hits were either covers or sappy or dopey, he spent enough time around people more famous than himself that he has something of a reputation as a hanger-on, and his career can look, from a distance, like one long act of self-sabotage. (It hasn't helped his reputation that he barely ever played live until he was long past his prime.) But he was also an astonishing iconoclast -- imagine what it would have taken in 1972 for an artist who'd just had a Top Five album to follow it up with the NSFW chorus of "You're Breaking My Heart," below -- and his influence keeps echoing in surprising places in alternative music.

Nilsson started his recording career in the early '60s, making singles under the names Johnny Niles and Bo Pete. His first record to make much of an impact, though, was 1967's Pandemonium Shadow Show, which got him into the Beatles' inner circle. That was also the album that established Nilsson as someone who could write successful songs for other people -- Tom Northcott's version of Nilsson's autobiographical "1941," below, grazed the bottom of the Hot 100 just a few months later.

When Nilsson had a hit of his own, it was a cover of someone else's song: Fred Neil's "Everybody's Talkin'." Nilsson's version owes a lot of its fame to its a prominent place in the movie Midnight Cowboy -- here are the bits of the movie where it's used.

"One," written by Nilsson for his 1968 album Aerial Ballet, was most famously covered by Three Dog Night the next year, but Filter surprisingly covered it for the X-Files soundtrack in 1998, and even made a video for it.

"Rainmaker," from his 1969 album Harry, opens with a brief drum solo (by Jim Gordon) that's become a familiar breakbeat among hip-hop producers over the past twenty years or so -- its earliest major use seems to have been Cypress Hill's 1993 "I Ain't Goin' Out Like That."

The Point, from 1971, was an animated TV special (and album) with a soundtrack by Nilsson, about a round-headed boy in a land where everything has to be pointed. Its theme song, "Me and My Arrow," has been covered by AM and Adrian Belew, among others, but it also reappeared in 2002 in another hip-hop context: sampled at length in the title track of Blackalicious's album Blazing Arrow.

1971's Nilsson Schmilsson album included a handful of songs whose fame has outlasted his own. One is his cover of Badfinger's "Without You," from which Mariah Carey adapted her 1994 version. Another is his novelty hit "Coconut," whose chorus refuses to die -- it turned up, for instance, in Tyga's 2008 collaboration with Gym Class Heroes' Travis McCoy, "Coconut Juice."

Nilsson's original song "Jump Into the Fire," from the same record, became one of LCD Soundsystem's favorite encores; here's LCD's performance from their final show, two years ago. (There's also a version recorded by the pre-Polyphonic Spree band Tripping Daisy.)

In 2006, the Walkmen covered Nilsson's 1974 album Pussy Cats -- during the recording of which Nilsson ruptured a vocal cord -- in its entirety. Here's their version of "Mucho Mungo," a song co-written by Nilsson and the album's producer John Lennon.

Neko Case picked up on the same album's heartbroken "Don't Forget Me," recording it on Middle Cyclone and playing it on this 2009 TV performance.

The last couple of decades of Nilsson's life weren't nearly as musically productive as that extraordinary 1967-1974 period, and not many artists have tried to reclaim his later songs. But he was ahead of his time in a lot of ways (he even recorded one of the first remix albums, 1971's Aerial Pandemonium Ballet), and there are still things he tried in his prime that nobody else has attempted, for better or worse -- like singing the closing credits of the 1968 movie Skidoo.