1. Grandaddy, "Summer… It's Gone"

In spite of the changing sunlight and daylight hours, we try to fight the transitioning seasons until one day we give up and admit it: Summer's gone. For some, that means no more than a wardrobe change. For others who live in vacation locales, it means boarding up, locking the doors, and heading back to colder, more urban, inhospitable climes. As Grandaddy laments, "Summer, it's gone and now it's clear / That no one is showing up here… / And so I turn away to head down roads / Dead ends and holes / And crowds of fools with common colds." The fuzzy, folksy Modesto band treats the changing seasons in this song with the normal reactions: anger, wistfulness, and resignation.

2. Gwen Stefani, "Early Winter"

The chilly heartbreak in "Early Winter" is evident not just in the churning lyrics or in Gwen Stefani's tormented coo—it works into the weather of the song itself, literally. Over brooding synth figures and against a strange electronic wind, Stefani sings "I always was one for tears" before suddenly swerving into reportorial mode with as much surprise as suits the situation: "The song's getting cold—it's snowing. It looks like an early winter, for us." Some references claim it's "the sun's getting cold…," but the way it genuinely sounds plays out better as a clever conceit that finds her shivering inside the song and striving desperately to get out.

3. The Dismemberment Plan, "Spider In The Snow"

A chilly, sickly sounding downer in the midst of one of the most amazing records of the '90s—The Dismemberment Plan's Emergency & I—"Spider In The Snow" recounts a brutally lonely time, with forgotten friends, a yawning pit, and ghosts ruining everyday life. "How can a body move at the speed of light and still find itself in such a rut?" asks Travis Morrison. And when does the cold, cold action take place? "As winter froze the life out of fall," of course.

4. The Rolling Stones, "Winter"

Sometimes the seasons don't change fast enough. On "Winter," Mick Jagger sings about looking forward to the "long, hot summer" when the "light of love will be burning bright." But he makes the line sound like the hope of a man stuck somewhere cold for the foreseeable future. He certainly wasn't in California "when the lights on all the Christmas trees went out," and wherever he is now, the string section that blankets him on this standout Goats Head Soup track clearly doesn't provide the warmth he needs.

5. Elvis Presley, "Snowbird"

Anne Murray first had a hit with this song in 1970, but there's no better version than the one found on the classic 1971 album Elvis Country, which gives the heartbreak a tone of manic desperation. Like poor Mick Jagger, Elvis is stuck somewhere cold while his love has fled, presumably for a more temperate climate. That leaves only Elvis and a snowbird to deal with the snow. "Spread your tiny wings and fly away," Elvis begs, but the snow, the bird, and the accompanying sadness seem unlikely to disappear soon.

6. The White Stripes, "Dead Leaves And The Dirty Ground"

Its title recalls the worst of the autumn-into-winter weeks, but most of The White Stripes' "Dead Leaves And The Dirty Ground" sounds fairly upbeat: Jack White praises his love to a hyperbolic degree ("Every breath that is in your lungs is a tiny little gift to me"), and he can't wait to get home. But when he does, she isn't there, and there's no one to wrap his arms around. Sigh.

7. Red House Painters, "Have You Forgotten"

In a sad song by a band that made sadness something to be prized, a meditation on what it means to grow old and numb runs against memories of how significant and charged just about everything proves in youth. "When we were kids, we hated things our parents did," sings Mark Kozelek. He goes on to catalog a few stock memories—listening low to Casey Kasem's radio show, times when friends were nothing more complicated than nice—before moving into a seasonal shift: "The smell of grass in spring… In October, leaves cover everything." Just like that, he passes through the better part of a year with simple words ready to sniff and feel crunch underfoot.

8. Teenage Fanclub, "December"

Most of the lyrics in this melancholy power-pop gem from Teenage Fanclub's Bandwagonesque don't make a lot of sense ("My mind is full of several things resembling a thought"), and the lyrical payoff isn't too direct, either: "I wanted to assassinate December." Still, anyone who's lived in wintry climes can relate to the sentiment.

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9. Lee Hazlewood, "My Autumn's Done Come"

Lee Hazlewood had the voice of a grumpy old man even in his youth, which helps sell this song about the pleasures of giving in to old age and death. "Let my blood pressure go on its way," goes one line—but there are upsides to letting yourself go. You get to drink and smoke all you want, and if anyone disturbs your time on a "hammock between two big trees," you have license to curse them out. You're grumpy and old. What are they going to do?

10. The Trade Winds, "New York's A Lonely Town"

New York's a great place to be a teen, right? The bustle, the excitement, the energy—what could be better? Well, the surfing, for one, as made clear by this 1965 song about a California boy pining for the West Coast when he realizes just how few opportunities he has to shoot the curl since his parents packed him up for the Big Apple. Even his car is feeling the pain. "I feel so bad each time," the chorus goes, "I look out there and find my woodie's outside covered with snow." A minor hit in its day, this Beach Boys-inspired song came courtesy of Peter Andreoli and Vincent Poncia Jr., a pair of songwriters from Rhode Island, a state not famed for its surfing.

11. Prince, "Sometimes It Snows In April"

Occasionally the seasons' refusal to change brings the most pain. Prince closed his 1986 album Parade with this tender ballad to a lost friend named Tracy, who died in spring, ruining the whole season. "Now springtime only reminds me of Tracy's tears," he sings, while noting that sometimes it snows then anyway. Ignore the fact that "Tracy" is "Christopher Tracy," Prince's alter ego in the not-so-beloved movie Under The Cherry Moon—and that the whole thing could be interpreted as Prince exploring how sad it would be for others if he died—and you might be moved too.

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12. The Motels, "Suddenly Last Summer"

A number-one hit in 1983, this Motels song almost certainly has nothing to do with Tennessee Williams. In fact, the lyrics make it tough to parse what it is about. "One summer never ends," Martha Davis sings, "one summer never begins." But the mood says what the words can't: Davis sounds trapped between seasons, wishing for a time that's unlikely to return as she loses herself between tinny beats and sad synths.

13-14. Simon And Garfunkel, "Leaves That Are Green" and "April, Come She Will"

"Feelin' Groovy" aside, much of Simon And Garfunkel's repertoire had a melancholy autumnal feel, in particular thanks to Garfunkel's harmonies. His voice often had the sweet, high, chilling effect of a one-man boy choir. But few of their songs are as delicately sad as "April, Come She Will" and "Leaves That Are Green," which both draw on seasonal imagery to mark the tragic passing of time. "Leaves" illustrates how love dies by watching how the seasons change: "And the leaves that are green turn to brown / And they wither with the wind, and they crumble in your hand." The simple final verse reduces all human interaction to a series of repetitive, unremarkable hellos and goodbyes, and repeats "That's all there is / And the leaves that are green turn to brown." It's Kurt Vonnegut's "So it goes" in song form. Similarly, "April" mournfully describes how "a love once new" grows old by quietly counting off the months from April to September, and attaching chilly imagery to each of them. Only Simon And Garfunkel could so effectively make summer seem like a shivery season.

15. The Mamas & The Papas, "California Dreamin'"

Written in the middle of the night in the dead of a dismal New York winter, "California Dreamin'" represented, in literal terms, the other side of sunshine pop. After an opening salvo of baroque guitar, the laconic tambourine beat and slow-rolling bass make for easy wallowing in the kind of melancholy that only comes with severe, season-induced geographic longing. And when that forlorn flute solo arrives, it's near impossible not to be transported to the wrong side of the windowpane, gazing out at a mockingly duochromatic (brown leaves, gray skies) landscape. Fittingly, the song's success secured John and Michelle Phillips' place in the land of their dreams. Happiness, however, proved more fleeting.

16. Jens Lekman, "Maple Leaves"

A bittersweet song about the heartbreak of trying to love someone who's all but given up on life, "Maple Leaves" is full of missed connections and little misunderstandings. Maybe it's because Jens Lekman's self-loathing lover is talking between jags of crying into his sheets, or maybe it's just a speech impediment, but Lekman laments that he never understood what she was so upset about: When she says it's "all make-believe," he thinks she's talking about "maple leaves"; when she mentions "the fall," he's unsure whether she means the season or the post-punk band. Adding to the melancholy, Lekman sets the scene by mentioning that it's "autumn in Gothenburg," where "rain falls hard on the city, on every homeless kitty."

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17. Scott Walker, "Winter Night"

Scott Walker's baroque string arrangements and pain-filled croon can make any song sound like the dead of winter, but he calls the season by name with this brief ode to a would-be lover who's so cold and unyielding, she's "like a winter night." Conjuring a snowy bleakness straight out of Jack London, the object of Walker's unrequited affection is icy and distant to the point that even her "thoughts are frozen," while her "eyes are lanterns growing dim" that he knows he'll never be able to light up. You can practically hear anguished wolves howling in the distance.

18. Chad & Jeremy, "A Summer Song"

The biggest hit from British Invasion duo Chad & Jeremy, 1964's "A Summer Song" got a second life 35 years later on the Rushmore soundtrack. With gentle, Simon And Garfunkel-esque harmonies and a delicate melody, the song was a perfect fit for a Wes Anderson film; wistfully nostalgic lyrics were just the icing on the cake. Produced by Shel Talmy (The Kinks, The Who), "A Summer Song" breezily recalls the quiet pleasures of summer, then takes on a tone of yearning and remorse at the refrain: "They say that all good things must end someday / Autumn leaves must fall."

19. Robyn Hitchcock, "Autumn Is Your Last Chance"

Robyn Hitchcock has always been autumnal in his outlook, with themes of death and organic decay pervading his music, perhaps never more strongly than on his 1984 classic I Often Dream Of Trains. In this quietly ethereal song, Hitchcock walks through a forest and ruminates on the fact that the beautiful blaze of fall colors is also a sign of the cold and darkness to come. Not coincidentally, he's also thinking about a relationship that's ended, and the palpable sense of absence left behind. "The leaves have never looked as good as now they're going to die," he sings, then enigmatically adds a gently devastating kicker: "But I know why."

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20. Reaching Quiet, "Broken Crow"

A one-off collaboration between Why? frontman Yoni Wolf and producer Odd Nosdam, Reaching Quiet's In The Shadow Of The Living Room was recorded in the members' old Ohio bedrooms shortly before they gave them up for good. "Broken Crow" bleeds small-town claustrophobia, sinking deep under thick drifts of static and synth as Wolf's painstaking attention to domestic minutiae paints an ever-retracting portrait of a Cincinnati winter. After warning his brother to "get out of here by December," he injects the bleak dirge with a daub of sickly color: "By the time the snow is melting / They always find four or five bodies hanging by belts / From the train trestles / Or in empty parking lots / Slit wrists turning what's left of the snow into cherry slushy." Sure, you can always go home again, but bring a duffel bag of salt and a bottle of Paxil.

21. Tom Waits, "November"

Given the bloody prominence of hunting on Tom Waits' The Black Rider, it's unsurprising that this song—propelled by a mournful, keening musical saw—contains some violent imagery. But Waits ramps up the seasonal-depression theme to ridiculous levels. November isn't just a month, it's his mortal enemy: "You're my firing squad, November," he gasps, urging the whole month to "go away, blow your brains out." Midway through the song, he yearns for the change of seasons as if his life literally depends on it, singing, "November has tied me to an old dead tree; get word to April to rescue me."

22. John Wesley Harding, "Sussex Ghost Story"

John Wesley Harding's "Sussex Ghost Story" is po-faced Victoriana with an eerie kick—Harding's unnamed narrator kills his wife, but beats the rap. Settling down with a schoolteacher, the happy couple spend "the summer of the year in a life of such perfection." But winter rolls around, and with that, "the cold of her rejection."

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23. Nick Drake, "Time Of No Reply"

Nick Drake's entire catalog defines the term "autumnal," but on this 1968 acoustic meditation—one of Drake's best songs, though it never made it onto his three proper albums—Drake uses the season as a metaphor for his own well-documented loneliness, melancholy, and restless spirit. "Summer was gone and the heat died down," Drake begins in that inimitable voice. Though he wouldn't see his own final change of seasons for six more years, lyrics such as "Time goes by from year to year / And no one asks why I am standing here" forecast what a lonely time that would be for this misunderstood genius.

24. Death Cab For Cutie, "Photobooth"

Summer flings aren't always carefree, especially when sobering fall air arrives a couple of months later. Death Cab's "Photobooth"—from a record tellingly titled The Forbidden Love EP—seems to offer a post-mortem on a tempestuous relationship that peaked "when the days were long," but now "as the summer's ending / the cold air will rush your hard heart away." Come fall, little remains except some photo-booth pictures, empty bottles, and spent cigarettes: "So pack a change of clothes, 'cause it's time to move on."

25. Jets To Brazil, "In The Summer's When You Really Know"

The change of seasons has provided songwriters with neat metaphors for ending relationships for ages, but Jets To Brazil frontman Blake Schwarzenbach takes it to another level of wistfulness on this track from 2000's Four Cornered Night. Summer is not only a season, but a state—and when the season rolls around, nice weather reveals a mortally wounded relationship: "In the summer, you really know / that it doesn't feel like summer so much anymore." Schwarzenbach isn't ready to give up, but he knows it's too late: "In the summer you'll really know / you're the only summer that I think I'll ever know."

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