A Century of Song is an attempt to summarize 100 years of popular music through 1000 carefully chosen tracks. Included within this list are landmark singles, stellar album cuts, huge hits, hidden gems, and more than a few personal favorites. Read the introduction for the project here, and enjoy the embedded videos and Spotify playlist.
“Sign o’ the Times”
Following the dissolution of The Revolution, Prince set out to make his most ambitious artistic statement yet. The resulting album, Sign o’ the Times, was a double-LP, immediately acknowledged by many critics as superior to Prince’s decade-defining 1984 record, Purple Rain. The album’s opening title track was its most immediately gripping song.
Working without a backing band, Prince took advantage of the wide-ranging capabilities of the Fairlight CMI synthesizer on “Sign o’ the Times.” The track’s raw, bare-bones instrumentation helped to pull attention toward Prince’s lyrics, which addressed drug abuse, violence, and the AIDS epidemic in one of the most socially conscious songs of his career.
Released two months before The Beatles announced their breakup, “Instant Karma!” effectively launched John Lennon’s career as a solo artist. While Lennon had already released three experimental records with Yoko Ono – plus the anti-war single “Give Peace a Chance” – “Instant Karma!” was an honest-to-goodness rock single that sounded like nothing short of an artistic rebirth.
Lennon is in fine voice on “Instant Karma!” – delivering a raw and spirited performance that stands alongside his best work. Musically, the song is uncomplicated, but it is given ample jolts by the drum fills of Alan White, and the celebratory, sing-along nature of its anthemic chorus.
“Such Great Heights”
A collaboration between Death Cab for Cutie vocalist/songwriter Ben Gibbard and electronic producer Jimmy Tamborello (aka Dntel), The Postal Service’s one-off album, Give Up, was one of the 2000s most unexpected success stories. Few songs better exemplify the decade’s crossover of indie music into the mainstream than the album’s first single, “Such Great Heights.”
Tamborello’s ethereal introduction would become instantly iconic, and much copied – as would his quickly skittering rhythm. Gibbard’s melancholic vocals might not have seemed like an ideal fit on paper, but his lonesome delivery and sentimental lyrics work surprisingly well in the track’s spacious environment.
With her fifth album as Weyes Blood – 2019’s Titanic Rising – Natalie Mering achieved a long overdue critical and commercial breakthrough. Finding its way toward the upper reaches of many year-end critics’ lists, Titanic Rising was a showcase for Mering’s musical and songwriting talents, and nowhere more so than on the album’s gorgeous first single, “Andromeda.”
Finding points of reference in “Andromeda” is easy. Mering’s vocals recall those of Joni Mitchell. Her production work comes off like a modernist take on the Laurel Canyon sound. As an added bonus, there’s a wonderful, George Harrison-esque slide guitar that runs throughout the track. While these comparisons establish a link between Weyes Blood and past greats, “Andromeda” coalesces into something truly unique and thoroughly engrossing.
For their third album, The Velvet Underground largely abandoned the bleak settings of 1968’s White Light / White Heat. Decamping to Hollywood’s TTG Studio’s – where three tracks from their epochal 1967 debut had been recorded – the notoriously subversive band would recast themselves as something of a chamber pop group on The Velvet Underground.
Much of The Velvet Underground’s mid-career reinvention has been attributed to Doug Yule, who replaced the experimentally minded John Cale following White Light. After all, it’s Yule’s understated vocals that first greet listeners on the album’s gentle breeze opener, “Candy Says.” However, the record also found Lou Reed further exploring the more sentimental side of his songwriting that had occasionally revealed itself on The Velvet Underground & Nico.
“Candy Says” is undoubtedly one of Reed’s most affectionate pieces of songwriting, but it wouldn’t be a Reed classic without his signature sly embrace of a social taboo. Written for Candy Darling – one of Andy Warhol’s “Superstars” – the song explores the then-little-discussed concept of gender dysphoria. “Candy Says” would be the final song that Lou Reed ever performed in public – just months before his 2013 death from cancer – in a guest appearance with the transgender artist ANOHNI. While it may lack the polish of the immaculate studio version, I’ve included the video of Reed’s touching final performance here.
Sigur Rós can do intimate and grand, but rarely do they straddle the line between the two descriptors as perfectly as on this highlight from 1999’s Ágætis byrjun. The album – whose title translates to “A Good Beginning” – found the Reykjavík group dramatically improving upon their 1997 debut Von, refining their sound into one of the most compelling in contemporary music.
“Starálfur” is built upon an acoustic arrangement – wonderfully captured in the live version from the band’s 2007 concert film, Heima. Accentuated by a lush string arrangement, the song takes on a deeper emotional resonance – one that made it a perfect fit for the most poignant scene in Wes Anderson’s 2004 film, The Life Aquatic With Steve Zissou.
“Sunday Bloody Sunday”
Famously introduced by Bono in live performances as “not a rebel song,” “Sunday Bloody Sunday” was U2’s most overt dive into politics to date – serving as the opening track to 1983’s visceral War. Largely stripping away the air of mystery that resonated throughout their earlier recordings, War was a biting, immediate work that took on an additional urgency in a live setting.
A rousing highlight of those live performances, “Sunday Bloody Sunday” balanced Bono’s plea for peace with a particularly aggressive performance from his bandmates. The continuation of “The Troubles” that inspired the song would keep “Sunday Bloody Sunday” a staple of U2’s live shows for years to come. It was the particularly impassioned 1987 performance from Rattle and Hum – hours after the Remembrance Day bombing in Enniskillen – that so captivated a younger me. I certainly didn’t understand the politics behind it at the time, but I was drawn to its intensity, nevertheless. I’ve included that version here.
“In a Mist (Bixology)”
Bix Beiderbecke was an immensely talented cornetist – considered by many to be the only contemporary rival of Louis Armstrong. In addition to his instrumental prowess, Beiderbecke was also a skilled composer – a talent that he honed on the piano. For many fans, it is Beiderbecke’s lone recorded piano performance that looms largest in his legacy.
Recorded in 1927, “In a Mist” displays a nuanced compositional skill that lands somewhere between jazz and classical music. Beiderbecke recorded the song solo, in a take that almost sounds like an afterthought in comparison to the more orchestrated tracks that he was typically associated with. The song would ultimately become a jazz standard – one covered by countless artists in the decades following Beiderbecke’s tragic 1931 death at the age of twenty-eight.
“Pouring Water On a Drowning Man”
While James Carr was not one of the best-known practitioners of soul music, he was one of the most singular talents that the genre produced in the sixties. Though his career was sidetracked by multiple complications – not the least of which being the bipolar disorder that made live performances virtually impossible – Carr released one of the decade’s most striking R&B debuts with 1967’s You Got My Mind Messed Up.
Though many listeners understandably rate Carr’s original recording of Chips Moman and Dan Penn’s classic “The Dark End of the Street” as his best moment, I’ve always had a slight preference for the spirited “Pouring Water on a Drowning Man.” The track – which opens You Got My Mind Messed Up – features a powerful vocal from Carr, and vibrant brass that recalls the famous Stax label that had once turned Carr down.
The last track on the utterly perfect first side of 1985’s Hounds of Love, “Cloudbusting” is one of Kate Bush’s most intriguing compositions from both a musical and lyrical standpoint. Like most of Hounds of Love, it finds Bush making excellent use of the Fairlight synth, while tastefully augmented by acoustic drums and strings.
Lyrically, “Cloudbusting” is a vignette inspired by Bush’s fascination with the Austrian-American psychologist and inventor, Wilhelm Reich. Told from the perspective of his young son Peter, the song recounts Reich’s arrest at the hands of the American authorities, after his work had attracted great controversy. It’s a moving tribute from one eccentric talent to another.
Funk pioneers – and one of the first racially integrated popular bands – Sly & The Family Stone brought an element of positivity to their socially conscious songs. “Everyday People” – the first single from their extraordinary 1969 album Stand! – could effectively serve as the San Francisco group’s theme song.
The upbeat rhythm and blues instrumental backing could have made “Everyday People” a hit on its own, but the group vocals that reaffirmed the band’s family vibe only strengthened the song’s appeal. A plea for racial harmony and cooperation (“different strokes for different folks”), the song became an anthem as it moved to the top of the American pop charts in early 1969.
A solemn, self-deprecating track at the heart of 1997’s The Lonesome Crowded West, “Trailer Trash” is one of the most affecting moments in Modest Mouse’s discography. Lead vocalist/guitarist Issac Brock documents growing up in a broken home, and the residual impact that it had on his ability to forge lasting relationships.
After a repetition of the song’s first verse and chorus, Brock and his bandmates let their instruments do the talking. The second half of “Trailer Trash” might not match the ferocity of the tracks that surround it on The Lonesome Crowded West, but it succeeds in expressing the same angst as Brock’s lyrics.
Will Toledo has never shied away from introspection in his songwriting for Car Seat Headrest, and “Something Soon” is no exception. A vivid examination of the mental and physical toll of depression and anxiety, the song is among the most revealing moments in the solo project-turned-band’s catalog to date.
Originally recorded for 2011’s self-released My Back Is Killing Me Baby, Toledo revisited the song in full band mode for his 2015 debut for Matador Records, Teens of Style. The added band dynamic not only gave “Something Soon” a fuller, more anthemic sound, but also upped its emotional impact considerably.
“River Deep – Mountain High”
One of Phil Spector’s most dramatic production works, “River Deep – Mountain High” was also a vehicle for an extraordinary, powerhouse vocal performance by Tina Turner. Though the song failed to achieve massive success upon its initial release, it has gone on to become one of the most iconic recordings of its time.
Written by Spector, along with Ellie Greenwich and Jeff Berry, “River Deep – Mountain High” was something of an anomaly for Spector’s patented Wall of Sound production. Whereas his productions rarely broke past mid-tempo, “River Deep” breezes through at a brisk pace, growing more intense as it approaches the triumphant chorus.
The grandeur of Spector’s production could have easily overwhelmed a lesser vocalist, but Tina Turner was more than up to the task. While the single gave equal credit to her husband/partner Ike Turner – who had absolutely nothing to do with the production or performance – Tina absolutely owns the track, delivering a thrilling performance that was coaxed by Spector’s notorious perfectionism.
“The Only Living Boy in New York”
The deep cut most loved by Simon & Garfunkel fans – perhaps only considered “deep” because of its absence from the duo’s billions-selling 1972 Greatest Hits compilation – “The Only Living Boy in New York” stands among the most affecting songs by the folk duo. Released on their final album together – 1970’s Bridge Over Troubled Water – the song also appeared as the B-side to their hit “Cecilia.”
As was often the case with Simon & Garfunkel, Paul Simon does most of the heavy lifting on “The Only Living Boy in New York.” However, like most of their greatest work together, the song reaches transcendence with the introduction of Art Garfunkel’s ethereal harmonies. His mostly wordless vocals in the song’s verses and bridge make for what is arguably the most delicately beautiful track of their career together.
“Doo Wop (That Thing)”
Surprisingly, following the breakout success of their sophomore album – 1996’s The Score – the hip-hop group Fugees broke up, leaving their three members to pursue solo endeavors. Unsurprisingly, the most fruitful of those endeavors – by a long shot – was the debut solo album from vocalist Lauryn Hill. Eventually earning multi-platinum status, critical acclaim, and a boatload of Grammys, The Miseducation of Lauryn Hill was an instant classic that remains one of the most iconic records of its time.
The album’s lead single, “Doo Wop” was similarly successful – reaching #1 on the charts, and drawing considerable praise for its clever juxtaposition of past and present styles. Undeniably memorable, with a fantastic beat and plentiful hooks – plus an engaging message to boot – the song showed the considerable range of Hill’s talents as a writer, performer, and producer.
“I Wanna Be Your Dog”
Though The Stooges were an important link in the slow evolution from garage rock to punk, there was something decidedly different about the Detroit band than anything that had come before. While difficult to pinpoint – a combination of their primitively raw musicianship alongside a penchant for nihilism – that difference is what would make The Stooges such a critical influence on so much that would follow in their wake.
It’s that nihilism which defines the most striking – and notorious – song from the band’s 1969 self-titled debut. Opening with a blast of saturated distortion from Ron Asheton’s guitar, “I Wanna Be Your Dog” lurches and clanks along to a metronomic piano and sleigh bell that cut through the fuzz. Iggy Pop’s lyrics are all submissive innuendo, designed to attract and repel in equal measure.
While The Jam emerged as a punk-adjacent band, the song that – for many – defines their career is one of the most musically reserved moments in their catalog. Appearing on the band’s fifth album – 1980’s Sound Affects – “That’s Entertainment” takes a unique approach to the concept of musical social commentary.
Written as a series of snapshots from Thatcher-era Britain, “That’s Entertainment” is simultaneously one of Paul Weller’s most vivid and compact compositions. Weller resists the urge to editorialize on his observations – aside from the repeated recitation of the song’s title – allowing the listener to come to their own conclusion as to the message of the scene he describes.
The low-key centerpiece to The Shins’ 2001 debut album Oh, Inverted World, “New Slang” is surprisingly dense, despite its modest exterior. James Mercer’s lyrics are knotty, matching the cryptic nature hinted at in the song’s title. Musically, his vocals remain understated, even when hitting the wonderful melodic turn in the chorus. They are complemented by Mercer’s own haunting, wordless backing vocals, which add a spectral dimension to the track.
“New Slang” was released as the first single from Oh, Inverted World. The song’s oft-mocked use in the 2004 film Garden State would help to make The Shins one of the poster bands for the gentle nudge of indie groups into the mainstream, but the song’s video – with clever nods to classic albums by The Replacements, Hüsker Dü, Slint, and Minutemen – confirmed the Albuquerque group’s devotion to the rich American underground scene from which they came.
“Thinkin Bout You”
Few debut albums are greeted with as much fanfare as that of Frank Ocean’s channel ORANGE. However, based on Ocean’s contributions to the Odd Future scene, prior collaborations with high profile artists, and his compelling backstory as a bisexual man in a notoriously homophobic industry, channel ORANGE was the rare debut whose release seemed like an “event” in real-time.
Another contributing factor to the anticipation that surrounded channel ORANGE was the release of its first single, “Thinkin Bout You,” three months prior. The song demonstrated Ocean’s songwriting capabilities, his penchant for minimalistic production, and as his ability to leap from a low croon to a brilliant falsetto. It was an auspicious start for an artist who would become one of the decade’s defining musical figures.