Knocked as a too-sensitive singer-songwriter type (back when that was considered a pejorative), James Taylor ended up defying the critics. And not just because he stuck around. Beginning with an embryonic start in 1968 with Apple Records, Taylor crafted a career filled with more than its share of sly humor and nifty little grooves to go with those admittedly frank confessionals and delicately constructed reminiscences. We've plucked a series of favorites from his self-titled debut, his '70s heyday and even a couple of late-period triumphs to fashion our list of the Top 10 James Taylor Songs.

  • 10

    'Something in the Way She Moves'

    From 'James Taylor' (1968)

    Recorded for the Beatles' boutique Apple label, this track – given a suitably prosaic late-'60s intro – would become a concert staple once it was stripped down to its essentials. Guests on Taylor's debut included Paul McCartney and George Harrison, who borrowed the title to jump-start a verse on his Beatles chart-topper "Something."

  • 9


    From 'That's Why I'm Here' (1986)

    Forget that national-anthem mishap. Taylor is an old pro at turning cover songs into radio hits – from the 1971 No. 1 "You've Got a Friend" (written by Carole King) and 1975's "(How Sweet It Is) To Be Loved by You" (Marvin Gaye) to 1979's "Up on the Roof" (also written by King with her then-husband Gerry Goffin). This late-period, and sweetly reimagined, Buddy Holly favorite reminds everyone why.

  • 8


    From 'Greatest Hits' (1976)

    Originally included on his 1970 breakthrough Sweet Baby James, this fun blues parody really comes to life on the concert version included on Taylor's first greatest-hits package six years later. With winking lines like "I'm a churnin' urn of burnin' funk," Taylor shows he's capable of more than just the earnest singer-songwriter stuff.

  • 7

    'Carolina on My Mind'

    From 'James Taylor' (1968)

    Taylor, who grew up in North Carolina, wrote this gentle remembrance while recording his debut album in London at the same time the Beatles were putting the White Album together. In later years, as with most of the songs that survived from this period of too-busy arrangements, Taylor smartly removed everything but his voice and guitar.

  • 6

    'Her Town Too'

    From 'Dad Loves His Work' (1981)

    Taylor collaborates with J.D. Souther (best known for his work with the Eagles) and Waddy Wachtel (Stevie Nicks, Linda Ronstadt and Warren Zevon), but the lyrics couldn't be more personal. Arriving as Taylor's marriage to Carly Simon fell apart, the song (as well as the album title) traces a surprisingly dark theme: "She gets the house and the garden; he gets the boys in the band."

  • 5

    'Country Road'

    From 'Sweet Baby James' (1970)

    A prototypical stroll through a blissfully pastoral landscape, "Country Road" seems to serve as a template for everything that would follow. Dig deeper, though, and the song turns out to be about the road that ran by McLean Hospital, where Taylor received treatment for depression five years earlier.

  • 4


    From 'Gorilla' (1975)

    On another of Taylor's impish delights, Graham Nash and David Crosby stop by to provide some of their stratospheric backing vocals to Taylor's story of a highly anticipated trip to Mexico that goes wrong because of a nasty case of Montezuma's revenge – supposedly based on a true experience. Still, he's compelled to return. Must be the margaritas.

  • 3


    From 'New Moon Shine' (1991)

    Taylor makes a deeply touching return to his youth in Carrboro, N.C., near Chapel Hill, on 1991's "Copperline." There's even a mention of his childhood dog Hercules playing in the eponymous Copperline, an area to the south of Chapel Hill. Part of the road that runs along Morgan Creek, also referenced here, was renamed the James Taylor Bridge in 2003.

  • 2

    'Don't Let Me Be Lonely Tonight'

    From 'One Man Dog' (1972)

    This jazz-inflected, intricately constructed romantic ballad features an intriguing narrative twist: Taylor inverts the typical lovelorn Tin Pan Alley stereotype by having the man portrayed as an abandoned lover. Taylor's lightly textured, deep-seated groove stands out – and it's something that would eventually move Eric Clapton to do his own growling version.

  • 1

    'Fire and Rain'

    From 'Sweet Baby James' (1970)

    There's a reason this is Taylor's best-known song and the obvious track to check in at the top spot on our list of the Top 10 James Taylor Songs: After all these years and albums, it remains his very best. A song about overcoming obstacles, perfectly matched for this age of worry, "Fire and Rain" still resonates as a moment of comfort and encouragement for anyone who's had troubles.

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