Gimmick? Avant-folk-rock-hip-hop hit? Slacker-rock hymn? Mocking satire of Generation X or Generation X-defining anthem? How do you define Loser? To Beck, it was a mediocre song that derided his rapping, and he only agreed to its release on the insistence of Tom Rothrock, who ran his label Bong Load. Yet it not only remains one of the weirdest, most surreal songs to have been a hit, it simultaneously managed to become an anthem for slackers, frat boys, and your mum alike. It raised the question of whether Loser would become an albatross around Beck’s neck, the one hit of the wonder. However, amid the debris of Beck’s sonic adventuring, Loser is a rather apposite introduction to his precocious talent: it has the samples (Johnny Jenkins’s cover of Dr John’s I Walk on Gilded Splinters), some blues slide guitar over shuffling hip-hop breaks and the enduring, nonsensical opening lyrics: “In the time of chimpanzees, I was a monkey.”

Another track from his debut album, Mellow Gold, but this one shows a different side to Beck: the contemplative, Delta blues guitar-playing gonzo raconteur. Here the magic is in the textures and the imperfections. This is Beck putting a modern twist on the blues tradition, its sloppiness and the fizz of the recording providing an enchanting intimacy. From the time he stumbled upon the New York anti-folk scene’s first wave in the late 1980s, Beck was influenced by the Delta blues, and this delicate, wiry guitar over a spectral, hypnotic melody, and some mumbled autobiographical lyrics, is a shaggy and moving embodiment of that spirit. The lyrics – meeting a girl, following her out to an island in Washington and getting a soul-destroying job washing dishes – gives us a rare glimpse into his life. There’s both resignation and hope there, and, with the line “I’ll be lonesome when I’m gone”, a real emotional punch in the gut.

From the hiss of needle on vinyl at the start and the “jigsaw jazz and the get-fresh flow”, this might be the song that best sums up Beck’s magpie influences. Freewheeling, inventive and irreverent, it’s a bewildering but beguiling mix of bizarre samples, an Afrika Bambaataa-style groove, a funked-out lounge-lizard keyboard line and a detuned holler of “I got two turntables and a microphone” – pilfered from Mantronix’s seminal electro 12in Needle to the Groove. The borrowing didn’t end there. The title and many of the spoken samples come from an obscure 1969 sex education album titled Sex for Teens (Where It’s At). It not only helped lift Beck into the mainstream, but by namechecking 70s outsider musician Gary Wilson (“Passing the dutchie from coast to coast / like my man Gary Wilson who rocks the most”), he helped to revive someone else’s career, too.

This song – a stopgap between the albums Odelay and Mutations – is taken from the soundtrack to A Life Less Ordinary, but don’t let that put you off. Beck said Deadweight, together with Tropicalia, was a part of his “Brazilian trilogy” (we’re still waiting for the third instalment). Yet unlike the bossa nova parping of Tropicalia, Deadweight’s Brazilian influence is woven together with a dusty, melancholic vibe to create an intoxicating brew. Sure, there’s the clockwork percussion of the vintage drum machines, the picked guitar and vinyl scratches, but the mood is set to a dusky mellowness. Beck tells us a hard-luck story about gambling and loneliness and not letting the sun catch you crying. It also acts as a fascinating link in Beck’s career, somewhere between the mishmash postmodern rock of Odelay and the downbeat psychedelia of Mutations. The song was nominated for best song from a movie at the 1998 MTV movie awards, but lost out to Will Smith’s Men in Black.

The sound of broken-hearted, disconsolate and psychedelic Beck, Nobody’s Fault But My Own, from Mutations, is the song you play as you sit in the dark of your room, rueing the day past. Even the title is dripping in introspection. When asked about the story behind the song, Beck said: “Well, I went down to my basement. It was raining outside, and I wrote it.” Over a gentle fog of sitar, synthesisers and strings (including viola courtesy of his dad, David Campbell), Beck’s earnest, maudlin delivery sees him tread softly between self-centeredness and doleful regret. There’s poetry here, too: “When the moon is a counterfeit / Better find the one that fits / Better find the one that lights the way for you.” Yet all its heaviness is leavened by the deftness of the orchestration, Nigel Godrich’s production and the beautifully wistful soundscape.

“I wanna get with you, only you, girl, and your sister. I think her name is Debra.” A staple of his live set for a long time – he had originally attempted to record Debra for Odelay but dropped it, thinking it was too flippant – this epic falsetto-led erotic funk ode to wooing a girl and her sister is Beck at his most brilliantly absurd. Though his fourth album Midnite Vultures is shot through with filth-funk satire, there’s no doubting Beck’s love and fascination for R&B, and R Kelly in particular. “These guys are singing R&B with a very sweet, smooth groove, but they’re singing about how they want to get some girl’s panties off and do them real good. It’s a really weird juxtaposition,” he said. From the opening line of “I met you at JC Penney / I think your nametag said Jenny!” there are some fantastic lines here, delivered with relish. Live, the song had always taken on a life of its own with Beck’s ad-libs sending the song into weird places and the band extending it into ridiculous lengths. “It became the centerpiece of the whole set. It was the song that people would react to more than the songs that they’d heard on the radio. So we kept playing it and playing it,” he said.

After all the junkyard postmodernist genre-borrowing, Beck’s fifth album Sea Change would prove to be his masterpiece. It’s easy to see why it was compared to Dylan’s Blood on the Tracks on its release: here, Beck laid everything on the line, with songs of heartbreak and resignation, influenced by his breakup with fiancee Leigh Limon. Yet it was a song he’d written years earlier that showed he’d possessed those skills all along: It’s All in Your Mind was recorded for the 1994 album One Foot in the Grave, ended up an outtake and was released as a 7in single the following year. It was only when Beck began strumming the song in the studio, that producer Nigel Godrich told him the song had to be included on the 2002 album. This re-recorded version is a rich tapestry of sounds, enhanced by melancholic string flourishes, courtesy of Beck’s father. As the music becomes more entwined, Beck, his voice deep and weary with sorrow, acknowledges “I wanted to be a good friend”, the stuffing completely knocked out of him. Anyone who’s been in a relationship will relate.

Girl shines through as one of Beck’s moments of pure, unashamed pop perfection. Shimmering and summery, from the 8-bit intro through to the effortless strum and “oohs” of the chorus, this is the sound of sitting in the sun drinking a piña colada from a coconut. Come on, there are even handclaps. But, of course, this is Beck and things aren’t that straightforward. What’s that he’s singing? “And I know I’m gonna steal her eye / She doesn’t even know what’s wrong / I know I’m gonna make her die / Take her where her soul belongs”, he coos over the sun-drenched chorus. If you’re feeling generous, these are heartfelt affirmations of lust; if you’re not, they’re the confessions of a homicidal stalker.

“Lord, please don’t forsake me. In my Mercedes-Benz,” sings Beck, referring back to Janis Joplin’s song. And you realise you never knew you wanted to hear him do classic rock until just now. Strange Apparition – part Gimme Shelter-era Stones-homage, part capitalist parodying hymn – is Beck playing the messianic rock star. The album it came from, The Information, which featured, among other bizarre things, a rambling conversation between Spike Jonze and Dave Eggers, saw Beck throwing everything into the mix, with varying degrees of success. On Strange Apparition, the clamouring, jangling percussion, piano and honking background vocals veer close to the grandiose (or the Dave Matthews Band, if you prefer). But in the breakdown for the bridge and the dramatic slow-motion ending, he shows his mastery. “I wanted it to sound like when the Beatles get out all their percussion and go bananas,” he explained.

Facebook Twitter Pinterest Winner … Beck accepts the best album Grammy award for Morning Phase from Prince at the awards ceremony earlier this year. Photograph: Kevork Djansezian/Getty Images

A decade after Sea Change came its spiritual heir. Morning Phase, a “companion piece of sorts” to the earlier album is, on the surface, another melancholy confessional. “There’s this feeling of tumult and uncertainty, getting through that long, dark night of the soul – whatever you want to call it,” Beck told Rolling Stone. “These songs were about coming out of that – how things do get better.” And that feeling of getting better shines through: much of Morning Phase bathes the songs in a shimmering glow, thanks to its orchestral grandeur and the guitars and strings shot through with warmth. It makes for an album that’s indulgent in a charming way. Nowhere is that more true than on the Dylanesque Blue Moon. So, while the opening line sees him cry “I’m so tired of being alone”, like an abandoned teenager, he’s ruminating on his loneliness over a lush backdrop of gorgeous guitars and sweet orchestration. You can almost see the light of the moon shining into his log cabin. As he sings “Cut me down to size, so I can fit inside”, the tenderness feels transcendental.