5 Hit James Taylor Songs That Crown Him As The Ultimate King Of Comfort

James Taylor has made a career of singing soft-rocking tunes with a voice so smooth voice it makes honey jealous. The soothing tone has been put to fantastic use on a slew of easy listening classics that fans turn to as audio comfort food. It's no simple task selecting a five-song greatest hits collection that best show off his laid-back pipes, but we decided to give it a go. It ended up being quite a relaxing task, much like listening to Taylor's tunes.

Our picks are some of Taylor's best-known works, in addition to being among his most successful singles. We chose tunes with topics that are perfectly suited for his cool delivery and chilled-out confidence, the secret formula that made the comfort king a standout in the world of easy listening. We think hits like "Handy Man" and "You've Got a Friend" deliver a message of support of both the romantic and the friendly kinds. "Your Smiling Face" and "How Sweet it Is (To be Loved by You)" offer reassurance that Taylor sells without coming off as casual or false. And the masterpiece "Fire and Rain" is a bravura performance that captures the existential angst of losing a friend, yet Taylor makes it feel like it's all going to be okay.

One of the most solemn and sober pieces in the James Taylor songbook, "Fire and Rain" tells the story of his friend taking her own life, a haunting tale told with such a delicate touch, it provided a guiding light for listeners grappling with grief of their own. This was more than simple musical comfort; it was solace offered by someone who could empathize and sympathize with others in a similar situation. Instead of just a song, Taylor offered a balm.

The existential tailspin the tragedy threw him into inspired this musical and poetic musing, resulting in a spiritual awakening and a surrender to the divine. It may be metaphorical more than literal, but the impact is the same. Taylor sharing his unsteadiness in the aftermath of loss has helped generations of listeners feel less alone in their own grief. It's not hard to imagine a line like "I always thought I'd see you again" is heart-wrenching enough to spur calls to friends and loved ones just to let them know how much they mean.

"Fire and Rain" lit up the chart for Taylor in 1970, peaking at No. 3 and becoming his first hit song. With an auspicious debut like that, the tunesmith had made a special connection with his audience that would last for decades.

The decades-long friendship between James Taylor and Carole King, the queen of the '60s and '70s singer-songwriter crowd, is represented beautifully by "You've Got a Friend," a King-written classic from her beloved "Tapestry" album that the troubadour gave his own sensitive spin. His reading is not far off from King's original, yet the disarming way the singer makes it his own reinforces the message that you really have a friend. No—seriously; you do. And he lives inside your sound system.

The two soft rock superstars have turned the tune into a duet many times through the years, performing it live at one another's concerts. It's become a signature song for Taylor, one of his best-known and most reassuring songs ever. It's also a perfect example of how this skilled musician adapts songs written by others and makes them feel as if they're his own creations.

Taylor turned "You've Got a Friend" into his one and only No. 1 single in 1971. It holds up as a timeless treasure that fans still turn to when they need a little assurance that they aren't alone in the world, something this easy listening icon has become renowned for.

James Taylor showed off his rollicking with this upbeat shuffle, a redo of Marvin Gaye's original Motown classic. Taylor gave his take on "How Sweet it Is (to be Loved by You)" a sing-along sensibility that encourages listeners to join in. You can practically see an adult contemporary audience swaying and clapping in time as they do their best to hit all the right notes. That's the kind of hootenanny feel-good energy Taylor captures in this self-penned treasure.

This is another one of those gentle reassurances that Taylor made his stock in trade. He sings about how much someone else has helped him feel good about his life, which in turn helps everyone else feel good, too. It's an audio feel-good fest that soothes the doubt and celebrates the happy vibes that don't depend on anything but the presence of your special someone.

The positivity helped shuttle the song to the No. 5 spot, giving Taylor a certified 1975 hit. It also gave boomers an apt wedding tune to dance to when it came time to turn up the tempo without losing the sweetness.

One of James Taylor's most comforting hits actually describes how much comfort his significant someone provides him. "Your Smiling Face" bops along with so much genre-defining yacht rock ease that you can practically taste the piña coladas and painkillers as you sing along. It may have only reached No. 20 on the Billboard Hot 100 when it showed up in 1977, but it's one of Taylor's most soothing tunes and a signature song that puts all of his special talents front and center.

There's no mistaking this mid-tempo jam for a slice of searing funk, but as James Taylor songs go, it might as well be a Bootsy Collins track. It's actually closer to Kenny Loggins or Michael McDonald, Taylor's fellow comfort rock kings. But "Your Smiling Face" is squarely in Taylor's wheelhouse, a jazzy lilt that consists of all curves and no edges, providing a gentle upbeat toe-tapper for folks who don't like to be jarred when they groove. Anyone who hears it will believe that Taylor is singing to them, which is sure to make their day brighter.

This one didn't reach heights as great as Taylor's other best-loved songs, but that's secondary to the warm glow it inspired in easy-rock lovers who still light up when they hear it. It's proof-positive that the comfort king has more than just gold records to back up his soft-rocking success.

"Handy Man" may be a double entendre that would sound creepy or lecherous if it were sung by a less trustworthy performer. Even the 1959 original by Jimmy Jones has an air of casualness that feels like a come-on. But when James Taylor sings it, he sounds like he's truly devoted to helping ladies repair the damage done by former lovers. Even a one-line description like that doesn't capture the soulful sincerity of Taylor hanging out his shingle to "fix broken hearts" because, as he professes, "I know that I truly can."

Maybe it's the way Taylor slowed the tempo down to a gentle gallop instead of the high-stepping Motown-like energy of Jones' version. It adds warmth and lets listeners absorb the lyrics as they roll by. "I'm not the kind to use a pencil or rule," he says, cleverly carrying on the smooth fix-it guy metaphor, "I'm handy with love and I'm no fool." Taylor's letting everyone know there's maturity behind the offer. And when he sings "I'm busy 24 hours a day"? Well ... let's assume he meant he'll be there regardless of the hour, but for only one sweetheart at a time.

The message resonated, and fans helped the song clock in at No. 4 in the peak soft rock year that was 1977. It also stayed on the Billboard Hot 100 for 20 weeks, handily making "Handy Man" Taylor's longest-charting single.