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320. Nick Cave & the Bad Seeds – “Into My Arms” (1997)

Borderline sappy, Cave’s classic love song is a shocking break from the material on Murder Ballads just a year before.


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319. The Jon Spencer Blues Explosion – “Bellbottoms!” (1994)

Their experimental blues was captured perfectly on this Baby Driver-featured zany classic that few have replicated.


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318. Juvenile (ft. Mannie Fresh & Lil Wayne) – “Back That Azz Up” (1998)

Maybe the only light in this doomed Democratic primary is seeing billionaire Tom Steyer awkwardly dancing on stage while Juvenile raps his classic for some insane amount of money.


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317. Wilco – “A Shot in the Arm” (1999)

Summerteeth featured Wilco’s most straightforward material, and this single was chief among them.


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316. Happy Mondays – “Kinky Afro” (1990)

The Britpop precursor of Madchester were best exemplified by the Stone Roses and Happy Mondays on their best material from Pills ‘n’ Thrills and Bellyaches.


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315. Herbert – “So Now…” (1998)

Here, frequent collaborator Dani Siciliano takes Herbert’s best production work into an electrifying example of futuristic pop.


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314. Annie – “The Greatest Hit” (1999)

Annie carried the Swedish pop legacy of The Carnivals with a further embrace of futuristic disco and a deadpan diva vocal approach.


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313. Third Eye Blind – “Semi-Charmed Life” (1997)

“All the Small Things” be damned, the true American pop-punk anthem is this “doo-doo-doo” classic. Play this and everybody imagines a pristine version of the late-’90s they want to go back to.


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312. The Roots (ft. Erykah Badu & Eve) – “You Got Me” (1999)

The Roots have always been an “album act,” but occasionally they can break out with a big hook brought on by someone like Badu here.


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311. Brandy & Monica – “This Boy Is Mine” (1998)

Less forced and awkward than the MJ/McCartney predecessor, this massive #1 hit acts as the best display of two of the biggest R&B stars of the time.


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310. My Bloody Valentine – “Sometimes” (1991)

“Sometimes” displays the most acoustic elements of MBV’s style on Loveless making it the most down-to-earth track on it.


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309. UGK – “Pocket Full of Stones” (1992)

For a major single off one of the first Southern Hip Hop classics, UGK sampled a couple of California hits to repurpose that “drive slow” vibe for a new locality.


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308. Dawn Penn – “You Don’t Love Me (No, No, No)” (1994)

Nearly 25 years after leaving the Rocksteady scene, Dawn Penn achieved major chart success with one of the best ’90s Reggae songs. The song is now a staple and a vital sample source in rap.


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307. Superchunk – “Slack Motherfucker” (1990)

Just barely a ’90s song, Superchunk’s first single under their own name was ahead of its time due to the oncoming mainstreaming of slacker alt-rock.


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306. Alice in Chains – “Would?” (1992)

Grunge bands could separate themselves by having a dynamic lead vocalist, and few were better than Alice in Chains’ Layne Staley.


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305. Lil Wayne (ft. Juvenile & B.G.) – “Tha Block Is Hot” (1999)

Lil Wayne has been doing this for a while, and even at this point, you couldn’t get away with saying he was just coasting on some stellar Mannie Fresh production.


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304. Sinéad O’Connor – “The Emperor’s New Clothes” (1990)

Overshadowed by one of the greatest pop songs ever, O’Connor’s second single off I Do Not Want What I Haven’t Got is aesthetically more in line with the art rock of her great previous album.


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303. Brain Eno/John Cale – “Lay My Love” (1990)

Here’s a perfect meeting place of genius: Eno’s underrated vocals & distinct guitar playing and Cale’s goddamn viola.


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302. Jay-Z – “Hard Knock Life (Ghetto Anthem)” (1998)

It seems weird to consider now, but in ’98, the jury was still out on whether Jay-Z could make a hit or was just a rapper’s rapper. With this Annie-sampling banger — and the equally-great “Can I Get A…” — that was laid to rest.


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301. Bruce Springsteen – “Streets of Philadelphia” (1993)

The best part of Demme’s film is the opening credit shots of the titular city with Springsteen’s most serene pop song soundtracking.


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300. Warren G – “This D.J.” (1994)

When you’re talking ’90s California classics, there’s The Chronic and then Regulate…G Funk Era. Warren G was a R&B/rap hybrid clearing the path for people like Drake.


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299. Refused – “New Noise” (1998)

When you name an album The Shape of Punk to Come, you have to follow through on a revolution. You can hear Fugazi in Refused’s sound, but a notable change is the larynx-bursting vocals coming from the alt-metal influence.


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298. Björk – “Unravel” (1997)

Back in 2006, Thom Yorke called this Homogenic non-single his favorite song ever, and it certainly ranks as one of Björk’s greatest vocal performances.


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297. Yo La Tengo – “Nowhere Near” (1993)

By the time Yo La Tengo released their first classic album with Painful, they had already had a full career with five albums. “Nowhere Near” took them into a dream pop world and gave them a distinct aesthetic.


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296. Pulp – “This Is Hardcore” (1998)

It was a long three years after Different Class and “Common People” for the Britpop world. Blur embraced American indie rock; Radiohead made OK Computer; Oasis released Be Here Now, the fastest-selling album in British history and more importantly, a massive failure in retrospect. Pulp relatively stayed the course with their seductive lounge rock and earned pretension.


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295. Le Tigre – “Deceptacon” (1999)

Le Tigre’s classic feels like an exercise in how many hooks to stuff in a three-minute pop punk song. Kathleen Hanna had a lot of practice in this field with Bikini Kill.


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294. Stereolab – “Ping Pong” (1994)

With an insane amount of classic albums, singles, and EPS in about a five-year span, Stereolab were the biggest act in avant-pop of the ’90s. The lead single on one of their classics Mars Audiac Quintet succinctly captures their under-the-radar greatness.


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293. Underworld – “Cowgirl” (1994)

When that “everything” starts repeating 30 seconds in, you know a progressive house classic is playing. Underworld were bold and brash, but they could back it up with some intense bangers.


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292. Foo Fighters – “This Is a Call” (1995)

Foo Fighters are now annoying in their rebranding as garage rock saviors, but on their first single, Grohl and co. proved to be a melodic rock force that would stick around.


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291. Wu-Tang Clan – “Shame on a Nigga” (1993)

The cascading piano and horns on the chorus from RZA might be his best production on 36 Chambers, and ODB lights up his verses with all he could muster.


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290. Bone Thugs-N-Harmony – “Thuggish Ruggish Bone” (1994)

Being the first single under their new name, “Thuggish Ruggish Bone” would cement Bone Thugs-N-Harmony’s status as the premier Horrorcore, R&B-embracing group of the ’90s.


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289. Black Star (ft. Common) – “Respiration” (1998)

Two of the smartest rappers ever got their start as Black Star and carried the Afrocentric spirit of the Native Tongues acts of the early-’90s. “Respiration” featured the equally-important Common and excellent production from Hi-Tek.


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288. The Auteurs – “Unsolved Child Murder” (1996)

This grim 2-minute baroque pop classic from Luke Haines is the understated greatest achievement of the Britpop leader.


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287. Modest Mouse – “Broke” (1996)

“Broke” proved Modest Mouse was capable of an album as good as The Lonesome Crowded West just a year later. This might be Isaac Brock’s best vocal performance.


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286. Belle & Sebastian – “The Stars of Track and Field” (1996)

Off the greatest chamber pop album of the ’90s and possibly all time, no singles were released. This was by design from Belle & Sebastian, who refused to sign to a bigger label to maintain creative control. It paid off, as songs like this opener bring them a beloved cult status that no amount of popularity can replace.


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285. LL Cool J – “Mama Said You Knock You Out” (1991)

A weird footnote: even as the title track and obviously the best song on the album, this was the fourth single and was released six months after the album’s release. Today, any exercise playlist without LL Cool J’s most beloved song is a lost opportunity.


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284. Guided by Voices – “I Am a Scientist” (1994)

Despite 30 studio albums, Guided by Voices’ reign could really be condensed into two back-to-back lo-fi classics (Bee Thousand and Alien Lanes). “I Am a Scientist” was the most notable track off the former.


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283. Big Pun (ft. Joe) – “I’m Not a Player” (1997)

Big Pun became a household name with this debut single that remains a East Coast hip-hop staple. Pun would only release one album while alive, but it was enough to make him a legend.


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282. Tortoise – “Djed” (1996)

Music was better when CAN’s spirit still lived on, and Tortoise was doing it better than anyone else in the ’90s. This 21-minute album opener thrived on some steady drumming and some patience from the listener.


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281. Björk – “Army of Me” (1995)

This “When the Levee Breaks”-sampling single rung in Björk’s rule with an iron fist.