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Valentine’s Day playlist: Classic songs of love and loss

A graphic depicting a gramophone playing music with he words "Collegian Playlists" coming out of it. Music notes float around in the space
(Graphic illustration by Abby Flitton | The Collegian)

Feb. 14 is arguably one of the most controversial holidays, depending on whether or not you’ve landed yourself a lover this year. Whether you need a soundtrack to gaze deeply into someone’s eyes or to blast while you angry-sob into your anime body pillow, The Collegian’s got you covered with some classic love — and breakup — songs for this Valentine’s Day. 

‘Be My Baby’ by The Ronettes


This upbeat pop classic exemplifies the peak of the ’60s girl group sound. Co-written and produced by legendary producer Phil Spector, the song had a major impact on other pop groups of the time, such as The Beatles and leading member of The Beach Boys, Brian Wilson. Spector is quoted as saying, “I’d like to have a nickel for every joint (Brian Wilson) smoked trying to figure out how I got the ‘Be My Baby’ sound.”

‘Don’t Worry Baby’  by The Beach Boys

Combining surf rock and layers of crooning vocals, “Don’t Worry Baby” is a sweet tune with a catchy chorus sure to leave your lover smitten and smiling. Beginning with a kick drum that echoes the opening beats of “Be My Baby” followed by a chorus of voices signature to The Beach Boys sound, “Don’t Worry Baby” has the same charming qualities that launched “Be My Baby” to the top of pop charts with a trademark Brian Wilson twist. 

‘Friday I’m In Love’ by The Cure

This hit track explores the ups and downs of an on-again, off-again relationship. Despite being released in 1992, the song has the energy to make the listener feel like the star of an ’80s coming-of-age movie, standing in the pouring rain outside their partner’s window. 

‘Harvest Moon’ by Neil Young

Switching gears and slowing down, Neil Young’s “Harvest Moon” is a tender folk tune perfect for an impromptu living room slow dance. The soft acoustic riff and surprisingly soulful harmonica can give the listener a sense of nostalgia for the present. 

‘Such Great Heights’ cover by Iron & Wine

This cover of The Postal Service’s “Such Great Heights” switches out the electronic pep of the original for a slower and more intimate acoustic sound. This more bare-bones approach brings out the beauty of the clever lyrics without the distraction of distorted electric drums and electronic melodies. 


With the sentimental and easily marketable stuff out of the way, it’s time to transition into the similarly expansive genre of heartbreak songs. 

‘I Wasted My Tears’ by Dolly Parton

Although lesser known than some of Dolly Parton’s hits like “Jolene” and “9 to 5,” “I Wasted My Tears” is a hidden gem in Parton’s discography and the epitome of ’60s country. Parton’s bright vocals shine over a chorus of background singers, a typical element of country production at that time. 

‘The Chain’ by Fleetwood Mac 

The entirety of Fleetwood Mac’s legendary 1977 album “Rumours” could be included on this list, with every track diving into the complex tangle of relationships that existed within the band. “The Chain” stands out as one of the best songs in rock ‘n’ roll, with its harsh kick that pierces through the mix and bluesy electric guitar contrasting with the twang of a Dobro. Every element of the song conveys the intense tension felt by the members of the band, the web of affairs and broken relationships, providing the fuel for this song’s raw energy. 

‘We Will Not Be Lovers’ by The Waterboys

This track may be unfamiliar to most readers due to its limited success in the United States, but the album it first appeared on, “Fisherman’s Blues,” topped United Kingdom charts upon its release in 1988. The instrumentation consists of a violent flurry of violins and a rich bass tone accompanied with occasional electric riffs. The incorporation of traditional Irish and Scottish styles in a rock context brings a level of power to the track that rivals even the heaviest distortion, perfectly accompanying the intense pull and inevitable heartbreak of a toxic relationship expressed in the song’s lyrics. 

‘Pictures of You’ by The Cure

So many songs by The Cure address the complexities of love and what it leaves behind that it felt justifiable to put them on here twice. “Pictures of You” has that raw emotional quality that so many songs in their discography share. Although the introductory chimes may be off-putting to listeners who associate them with a tacky sound, the lavish production is part of what gives this song its intense atmosphere. 

‘Don’t Speak’ by No Doubt

If you’ve never blasted this song after finding your mom’s old “Tragic Kingdom” CD forgotten in the crevices of your garage, you’re truly missing out on a cathartic experience. The fake romanticism of a Spanish guitar and string section in the middle of ’90s pop-rock gives the type of passion perfect for a top 100 breakup song.

Max Hogan can be reached at or on Twitter @macnogan.

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