The 50 best road trip songs of all time

Hit the road, Jack, and crank up the dial with our definitive list of the best road trip songs ever made

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40

“Jack & Diane” by John Cougar Mellencamp

Inevitably, your road trip is going to hit some lulls: You’re fighting off the yawns, your passengers have passed out, and it's 57 miles to the next pit stop. When this happens, there’s one sure-fire way to get your journey back on course: Unleash the Cougar. Indiana’s favorite son specializes in songs about the heartland, and his crowning jewel is this 1982 chart topper about two high-school sweethearts and the twists and turns of their American Dream. Despite the jaunty beat and an epic drum breakdown rivaling the one in Phil Collins’s “In the Air Tonight,” the tale is cautionary, urging us to savor those thrilling, carefree teenage years. Oh, to be young, in love and suckin’ on chili dogs outside the Tastee Freez.…—Michael Chen

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39

“Everyday Is a Winding Road” by Sheryl Crow

The little sister to Tom Cochrane’s “Life Is a Highway,” Sheryl Crow’s 1996 hit unabashedly co-opts the use of automotive byways as metaphors for life’s ups and downs. (Billy “the world is a vampire” Corgan apparently misread the memo.) The “wacky” characters in Crow’s songs are often a bit too precious for our liking—in this case, a vending-machine repairman with a daughter he calls “Easter” (what?)—but the chorus always gets us fired up for some hairpin turns, even when we’re cruising down a seemingly endless straightaway. The song works perfectly when your destination is San Francisco’s Lombard Street, whose residents probably have this tune swirling in their heads 24/7.—Michael Chen

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38

“Scar Tissue” by Red Hot Chili Peppers

The L.A.-bred Peppers clearly know a thing or two about hitting the highways, as evidenced by a song catalog riddled with Cali-inspired, crank-up-the-dial tunes. For a journey out on the open road, we like this lead track off the band’s 1999 album, Californication, due to its lilting desert-by-twilight vibe. The song’s main attraction is John Frusciante’s wailing guitar solos, which achingly embody Anthony Kiedis’s lyrics about isolation and the twisted, drug-fueled paths he’s traversed (“With the birds I’ll share this lonely view”). Enter tumbleweed, stage right.—Michael Chen

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37

“The Golden Age” by Beck

This 2002 tune, off Beck’s desolate, heartbreaking Sea Change, is one of the most perfect and profound illustrations of driving as a means of escape. It’s best played at night, in the desert if you’ve got one handy, when you feel like crap but have pretty much come to terms with it. And when, as Beck says, “You've gotta drive all night just to feel like you’re okay.” Go forth, drive and wallow. Maybe you’ll feel better in the morning.—Kate Wertheimer

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36

“Fast Car” by Tracy Chapman

Tracy Chapman’s beautifully direct 1988 hit, from her eponymous debut album, gives escapism an especially poignant twist. The speeding car and its romantic freedom (“City lights stretched out before us/Your arm felt nice wrapped 'round my shoulder”) can’t be separated from what it’s speeding from: a life of urban poverty, trapped taking care of deadbeats—first a drunk father and then, at the end, the very driver that she had dreamed might carry her away to her rescue.—Adam Feldman

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35

“Fade Into You” by Mazzy Star

Night driving found a shimmering musical complement in this ethereal 1994 track from dream popsters Mazzy Star. In a rare bit of sonic magic, it seems that no matter how fast you’re driving, the low beats per minute on “Fade Into You” always manage to sync up perfectly with the passing dividing lines visible from your car’s two headlights. And a night drive, preferably undertaken as you’re pining for an unrequited love, wouldn’t be complete without Hope Sandoval’s dusk, haunting vocals echoing throughout your ride. Two-lane highway bliss, by moonlight.—Michael Chen

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34

“Chicago” by Sufjan Stevens

Some songs make your heart beat faster from the get-go, and 2005 road-trip swoon “Chicago” is just such a gem, announcing its entrance in a whirlwind of strings and a rush of percussion. The backing cuts suddenly to Stevens’s voice, whispering that most universal human sentiment: “I fell in love again—all things go, all things go,” and then later, another familiar feeling: “I made a lot of mistakes, I made a lot of mistakes.” It’s this acknowledgment of our frailty, coupled with our irrepressible capacity for hope and excitement that gives “Chicago” its electrifying, driving charge. That and the fact it features in the ridiculously touching road movie Little Miss Sunshine.—Sophie Harris

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33

“I Drove All Night” by Cyndi Lauper

The irreverent thrift-shop spunk that defined Cyndi Lauper’s persona in the 1980s sometimes overshadowed her killer range and sensitivity as a vocalist, but “I Drove All Night”—from her third album, 1989’s A Night to Remember—finds her in a different mode. Driven by a feverish desire, she takes the wheel and makes her own way to her lover’s bed. (She may coyly ask, “Is that all right?” but by that time she’s already done it.) And Lauper’s impressively sustained last note is a perfect expression of the song’s sense of undeterrable yearning.—Adam Feldman

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32

“Two of Us” by the Beatles

The Fab Four’s back catalog is replete with songs about traveling around: “Drive My Car,” “Day Tripper,” “Ticket to Ride,” “Yellow Submarine”—the list goes on and on like a long and winding road. No Beatles track, though, captures the feeling of setting off into uncharted territory with someone special better than “Two of Us,” penned by Paul McCartney in 1969. There is debate as to whether McCartney’s partner in crime in this song is future wife Linda Eastman, as he claims, or John Lennon, which some of the nostalgia-infused lyrics would suggest. No matter—an impromptu road trip is a good time whether your passenger-seat companion is your new flame or your counterpart in the greatest songwriting tandem of all time.—Michael Chen

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31

“Running on Empty” by Jackson Browne

There's a reason this song soundtracks the Forrest Gump protagonist’s famous transcontinental jog: Few pop tunes capture the rush of earthbound travel—by foot, by car or, in Jackson Browne’s case, by tour bus—better than this autobiographical FM-radio staple. But what makes it a classic is the ambiguity in Browne’s message. “I don’t know where I’m running now; I’m just running on," he sings, perfectly summing up how the desire for escape can be its own kind of trap.—Hank Shteamer

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