“Sky Is Open” – The Long Winters

Even if you’re not headed somewhere you actually want to be, “Sky Is Open” from The Long Winters’ debut album does its job well of putting you at ease. As the harmonies rise to sheer exuberance, frontman John Roderick proclaims “I’m finally the highest bird,” and amid the soaring vocals, ringing bursts of guitar, and crisp lyrics depicting a retired pilot taking to the skies again, this cut finds the group hitting their stride thousands of feet in the air.

“The Only Living Boy In New York” – Simon & Garfunkel

For me, this song is forever connected with the utterly transcendent end of Zach Braff’s Garden State, but it’s just as gripping on its own, all rich harmonies and loose strums  of acoustic guitar backing the plaintively delivered, achingly simple lyrics (“Half of the time we’re gone and we don’t know where”). With its excellent build-up to a quiet, lulling fade-out, the pair has created a lush expression of loneliness and devotion across continents.

“Boston” – Augustana

Running on sheer hope – not to mention swaths of guitar and piano, a propulsive build-up, and Dan Layus’ emotive falsetto – Augustana’s ode to reinvention imagines that leaving sunny, imperfect California to the East would give meaning to everything else. A little naïve, sure, but it’s a fairly universal feeling to believe that putting roots elsewhere will be the change needed to jumpstart your life, and the San Diego pop rockers capture that perfectly.

“Run” – Collective Soul

“Run,” from the band’s 1999 release Dosage, really has nothing to do with flying, but the song’s downbeat mood of quiet longing always seems to couple itself well with the blissed-out rumination that seems to arise when you’re soaring above the ground.  Restrained but still heart-tugging, the subdued vocals and lovely melodies call up a blend of sheer, intuitive feeling that’s tough to put to words; it’s sad but uplifting, lonely but cathartic – simply, it’s perfect. 

“Different Names For The Same Thing” – Death Cab For Cutie

Death Cab For Cutie can churn out gorgeously melancholy gems like no other, and “Different Names For The Same Thing,” from their flawless major-label debut Plans (2005) doesn’t disappoint. Shifting halfway from a mellow, piano-laden ballad to a textured cataclysm of bells, drums, and piles of harmonies, this is an ambitious outing for Death Cab that nevertheless retains its sense of intimacy and warmth even as it reaches across to foreign waters.

“Homecoming” – Kanye West Feat. Chris Martin

Simultaneously earnest and slick, Kanye West’s “Homecoming” is a love letter to Chicago depicted through reminisces of his first relationship. With a hook silkily sung by Chris Martin, a plinking piano riff, and West’s characteristically blustering yet somehow sincere rhymes, this song embodies the mixed emotions of returning home again – uncertainty tinged with excitement, hoping the city you loved hasn’t changed even if you have – in its concise refrain: “Do you think about me now and then? ‘Cause I’m coming home / Coming home again.”

“Bright Lights” – Matchbox 20

Matchbox 20 has been churning out deliciously palatable pop (though not of the overtly cheesy variety) since the ‘90s, and I’m not ashamed to love it. “Bright Lights” is another hit for Rob Thomas: big hooky guitars, a melody that sticks in your head, and Thomas’s vocals that reach right for the heartstrings as they plead to his city-bound lover to “come on home.” All the tasty melodies in the world can’t disguise the song’s blatant yearning, the pull of distance and hearts suddenly halved – pretty substantial for a stylish pop group.

“In The Aeroplane Over The Sea” – Neutral Milk Hotel

I’ve made no secret of my deep soft spot for Neutral Milk Hotel, and the title cut from their breakthrough (and final) album is nothing short of brilliant. Featuring little more than acoustic guitar strumming and the eerie whine of a musical saw, “Aeroplane” melds Mangum’s surreal, evocative lyrics with a stirringly real final proclamation: “Can’t believe how strange it is to be anything at all.” It’s a song of youthful innocence, of seizing the day, and it’s always given me that heady, shining feeling of flight: soaring higher and higher, until nothing seems real, and you are free.

“Learning To Fly” – Pink Floyd

Of multiple tracks with similar names (Tom Petty, Foo Fighters, etc.), this Pink Floyd cut, from their 1987 Momentary Lapse Of Reason album, is a stunning, epic song, even from the masters of epic. The hauntingly visceral lyrics (“Above the planet on a wing and a prayer / My grubby halo, a vapour trail in the empty air”) are echoed by spacious, twisting instrumentation that calls up perfectly the sensation of flight (and David Gilmour’s guitar work is as full of feeling and technique as always).

“Spread Your Wings” –Queen

One of Queen’s less bombastic offerings, this John Deacon-penned track from News Of The World captures that aching itch we all know to “spread your wings and fly away / Fly away, far away.” With Freddie Mercury’s signature soaring vocals, rich guitar lines, and piano, the group strips away some of the glitz to create a rootsier, relatable song and another memorable entry in the Queen catalogue.