10 Underrated Songs That Deserve a Second Listen Again

by Johan Tobias

The world of music is a sprawling playground where tastes clash, trends rise, and some tracks slip through the cracks. In this roundup of 10 underrated songs we’ve dug deep into the archives—from the golden era of rock ’n’ roll to the glossy pop of the 2010s—to spotlight tunes that deserve a fresh listen, even if opinions differ wildly.

Why These 10 Underrated Songs Matter

11 G.R.L. (2014)

The 2010s ushered in a wave of hyper‑polished pop, but tucked away among the synths and auto‑tuned hooks sits the fierce anthem “Ugly Heart” by the girl group G.R.L. This track packs a punch with its driving beat and unapologetic lyrics, proving the decade wasn’t all sugary fluff.

Critics praised the song for its bold production and catchy chorus, yet commercial success proved fleeting. G.R.L. managed to snag a handful of radio spins before tragedy struck.

Tragically, “Ugly Heart” became the group’s final single before the heartbreaking loss of member Simone Battle, who took her own life on September 5, 2014, casting a somber shadow over the song’s legacy.

10 Dick Penner (1957)

The 1950s were dominated by icons like Elvis, Sinatra, and Johnny Cash, but few recall “Cindy Lou” by Dick Penner when reminiscing about that era. While the charts were filled with rockabilly and crooners, Penner’s tune slipped under mainstream radar.

Before penning “Cindy Lou,” Penner co‑wrote the classic “Ooby Dooby,” which later became a massive hit for Roy Orbison. A versatile talent, Penner wore many hats—singer, guitarist, recording artist, and even a retired English professor—adding depth to his musical pursuits.

Though he never matched the chart‑topping success of “Ooby Dooby,” Penner’s catalog, including “Move Baby Move,” “Fine Little Baby,” and “Honey Love,” showcases his knack for catchy melodies, with “Cindy Lou” standing out as a hidden gem from the rock‑n‑roll golden age.

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9 Simon & Garfunkel (1966)

Simon & Garfunkel are forever linked to timeless hits like “The Sound of Silence,” “Bridge Over Troubled Water,” and “Mrs. Robinson.” Yet “Cloudy,” a lesser‑known track from their 1966 album Parsley, Sage, Rosemary and Thyme, proves the duo’s range extended far beyond their biggest chart‑busters.

Co‑written by Paul Simon and Australian folk‑rock musician Bruce Woodley, “Cloudy” captures a whimsical, breezy vibe. Its lyrical imagery paints a picture of a narrator watching clouds drift across the sky, delivering a soothing, melodic experience that often goes unnoticed by casual listeners.

8 The Hollies (1971)

When The Hollies released “Long Cool Woman in a Black Dress” in 1972, they struck gold, selling two million copies worldwide and clinching the No. 2 spot on the Billboard Hot 100 for a solid two weeks. Its gritty, blues‑rock swagger set it apart from the band’s earlier pop‑rock hits.

Controversy soon followed when John Fogerty of Creedence Clearwater Revival sued The Hollies, alleging the song borrowed heavily from his “Green River.” The dispute settled out of court, awarding Fogerty a share of the proceeds.

Despite the legal drama, the track endures as a memorable anthem of the 1970s, celebrated for its driving rhythm and cinematic storytelling—a true testament to its underrated status.

7 Paper Lace (1974)

Paper Lace’s “The Night Chicago Died” sparked a political firestorm when it landed on Mayor Richard Daley’s desk. The mayor reportedly despised the song, with staff urging the band to “jump in the Chicago River” and repeat the stunt three times.

Fans remain split: some echo the mayor’s disdain, while others champion the track as an overlooked masterpiece. The narrative dramatizes a fictional showdown between Chicago police and Al Capone’s syndicate, opening with a synth‑driven siren that segues into spoken verses.

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6 Air Supply (1981)

Air Supply never claimed the title of “cool”—the band even admitted they weren’t MTV‑ready or Rolling Stone‑favorite. Yet their vocal prowess and melodic sensibility earned them eight U.S. top‑ten hits throughout the 1980s.

Inducted into the Australian Recording Industry Association Hall of Fame in 2013, the group’s catalog boasts power ballads like “Even the Nights Are Better,” “All Out of Love,” and “Making Love Out of Nothing at All.” Among these, “Sweet Dreams” shines as an underrated gem, blending tender lyrics with a subtle rock edge that showcases Russell Hitchcock’s soaring vocal range.

5 Tracy Chapman (1988)

Tracy Chapman’s résumé includes Grammy‑winning hits such as “Give Me One Reason,” “Fast Car,” and “Talkin’ ’Bout a Revolution.” Despite her global acclaim, Chapman’s softer ballads often receive limited airplay, leaving many of her nuanced tracks underappreciated.

“Baby, Can I Hold You,” released in 1988, failed to break into the U.S. Top 40, yet its heartfelt simplicity resonated worldwide. Boyzone’s 1997 cover propelled the song to No. 2 on the UK Singles Chart and secured its place as the 26th best‑selling single of that year, though the original remains the more tender, soulful rendition.

4 Tanita Tikaram (1988)

The line “All God’s children need traveling shoes,” borrowed from Maya Angelou’s book title, anchors Tanita Tikaram’s 1988 breakout “Twist in My Sobriety.” The song’s cryptic lyrics explore youthful introspection and the emotional turbulence of turning eighteen.

While it never cracked the U.S. market, the single surged into the top 10 across several European nations. Tikaram’s deep, resonant voice weaves through the melodic arrangement, delivering a haunting atmosphere that cements the track’s status as an overlooked classic.

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3 4 Non Blondes (1992)

Lead singer Linda Perry famously disliked the production choices for “What’s Up,” yet the band re‑recorded her demo in a single day, birthing a track that peaked at No. 11 on the pop chart. Its raw, anthemic chorus quickly became a radio staple.

Critics remain divided—some label it the worst song of the ’90s, while others champion its enduring appeal. In 2021, the official music video surpassed one billion YouTube views, reaffirming the song’s lasting cultural impact despite its polarizing reputation.

2 Deep Blue Something (1993)

The 1990s churned out a kaleidoscope of cultural moments, from iconic sitcoms to groundbreaking grunge. While tracks like “Macarena” dominated dance floors, a slew of lesser‑known songs quietly thrived.

Among these, “Breakfast at Tiffany’s” by Deep Blue Something emerged in 1995 as the band’s sole chart‑topper. Its lyrical inspiration draws from classic cinema—both “Roman Holiday” and the titular Audrey Hepburn film—blending nostalgic references with a catchy pop‑rock hook.

Although the group never replicated this success, the song remains a nostalgic staple for those who cherish ’90s one‑hit wonders, cementing its place as an underrated anthem of the decade.

1 Simple Plan (2002)

Simple Plan’s drummer faced parental resistance when pursuing a music career, a struggle that fueled the emotionally charged lyrics of “Perfect.” Bassist David Desrosiers echoed this sentiment, noting the track reflects his brother’s support during his own artistic journey.

Charting within the top 40 across Canada, the United States, Australia, and New Zealand, “Perfect” resonated with teens wrestling with familial expectations. Though its popularity has waned, the song’s raw honesty continues to strike a chord with listeners seeking solace in shared struggles.

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