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280. Beenie Man – “Who Am I” (1997)

One of the greatest Dancehall songs of the decade, “Who Am I” had an immediate influence on late-’90s Hip-Hop and is considered a template for today’s UK Grime scene.


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279. Soundgarden – “Black Hole Sun” (1994)

Soundgarden could play more aggressively and display Cornell’s vocals better, but “Black Hole Sun” still has the biggest allure through a stunning guitar riff making it the definitive non-Nirvana grunge single.


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278. Mariah Carey – “Vision of Love” (1990)

The debut single from the ’90s biggest artist was a #1 hit and deservingly so with a full display of Carey’s electrifying vocals and some flawless slow-dance production.


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277. Main Source (ft. Nas) – “Live at the Barbeque” (1991)

Main Source had one great album and launched the career of the producer Large Professor, but their most notable contribution was getting Nas’ first verse on record. Everything great he would display on Illmatic could be heard here three years earlier.


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276. B.G. (ft. Baby, Turk, Mannie Fresh, Juvenile, & Lil Wayne) – “Bling Bling” (1999)

This was the definitive Hot Boyz posse cut with Mannie Fresh going off, every rapper keeping it cool like nobody before, and Lil Wayne being weird on the chorus.


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275. Jeff Buckley – “Grace” (1994)

Gary Lucas was a member of Captain Beefheart’s band in the ’80s and became a frequent collaborator with Jeff Buckley on songs like this debut single. He’s credited with “magical guitarness” on the liner notes.


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274. D’Angelo – “Lady” (1995)

One of the biggest Neo soul hits of the ’90s, “Lady” is one of two songs that D’Angelo shared writing credits with Raphael Saadiq throughout his solo career. The other is “Untitled (How Does It Feel).”


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273. Nirvana – “Polly” (1991)

“Polly” is stylistically and lyrically bleak in a way that seemed to speak to Cobain’s internal struggles better than any Nevermind track.


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272. Eazy-E (ft. Dresta & B.G. Knocc Out) – “Real Muthaphuckkin G’s” (1993)

Eazy-E’s retaliation track to Dre’s “Fuck Wit Dre Day” became his highest-charting solo single before his death in ’95. A funny footnote is that the actor that portrayed and mocked Eazy-E in Dre’s video returns here to be brutally assaulted; the money was good, I guess.


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271. Stone Temple Pilots – “Interstate Love Song” (1994)

Whatever tiers of Grunge there are, Stone Temple Pilots will never be considered in the top one, but on this one song, Scott Weiland and Dean DeLeo crafted a perfect little gem.


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270. Snoop Dogg – “Who Am I (What’s My Name)” (1993)

Snoop Dogg’s first solo single might be Dr. Dre’s greatest production feat and made George Clinton’s classic “Atomic Dog” belong to Snoop forever.


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269. OutKast – “Player’s Ball” (1993)

OutKast’s first single was great, a Billboard top 40 hit, and brought the “Dirty South” hip-hop style to the mainstream. They would spend the next decade continually topping this, but it started here for the duo.


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268. Kool G Rap & DJ Polo – “On the Run” (1992)

“On the Run” is one of the best storytelling rap songs ever on the duo’s third underrated classic in a row. The story of mafioso rap is not complete without recognizing these two.


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267. Positive K – “I Got a Man” (1992)

This song is a classic due to the repurposed disco guitar of A Taste of Honey’s 1980 song “Rescue Me” and the fast-paced conversation style of rapping from Positive K as the man and woman (with pitched-up vocals).


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266. Cocteau Twins – “Heaven or Las Vegas” (1990)

I’m convinced that the English language is not being sung here or on any of Heaven or Las Vegas for that matter. I can read the lyrics and not only is there a phonetic disconnect, but there’s a spiritual one as well. These three were tapping into something way more ethereal here that remains indecipherable.


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265. Ice Cube – “The Nigga You Love to Hate” (1990)

The Bomb Squad produced two classic albums in 1990; Ice Cube’s debut is one of them. The first proper song on the album announced that Ice Cube was both the greatest and most confrontational rapper at the moment.


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264. Talk Talk – “Ascension Day” (1991)

Mark Hollis was so beyond the idea of “songs” by Talk Talk’s last album that it feels odd to single out anything from the avant jazz rock era. “Ascension Day” might have the best “pop” elements of any Laughing Stock track though.


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263. Beastie Boys – “So What’cha Want” (1992)

After the plunderphonics-spawning critical success of Paul’s Boutique, Beastie Boys did a 180° and legitimized rap rock for a new generation on Check Your Head. “So What’cha Want” is the only major single off the album.


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262. Hole – “Celebrity Skin” (1998)

This is Hole’s most commercially successful song and feels much larger and longer than its 2 minute and 42 second runtime.


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261. Jawbox – “Savory” (1994)

For Your Own Special Sweetheart might be the greatest post-hardcore album released through Atlantic Records and certainly only one of a few that sacrificed none of its street cred in the process. “Savory” received some MTV airplay, but the band would eventually be shipped off to an Atlantic subsidiary label and officially dropped by the next album. Ah, the ’90s.


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260. Mase – “Feel So Good” (1997)

The critical and commercial success of “Feel So Good” and Harlem World put Mase on a trajectory to be a major factor in the 21st century and beyond. Instead, Double Up from ’99 was a bit of a disappointment, and he would announce that he was becoming a minister.


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259. Stereolab – “Cybele’s Reverie” (1996)

Emperor Tomato Ketchup is Stereolab’s peak, and “Cybele’s Reverie” might be the only true standout on the consistently-great album. The digitized strings get more abrasive as the song proceeds.


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258. Palace Music – “New Partner” (1995)

Will Oldham made more critically-revered music in the decade, but “New Partner” is the closest he got to an accessible indie folk staple.


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257. House of Pain – “Jump Around” (1992)

In the early-’90s, artists really wanted you to jump. It wasn’t enough for you to stand; to prove your worth, you had to put that extra stress on your feet and knees. House of Pain requested this behavior from us better than anyone else.


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256. DMX – “Ruff Ryders’ Anthem” (1998)

DMX was the first rapper to release two #1 rap albums in the same year under the same year. “Ruff Ryders’ Anthem” stands as the go-to jam of DMX’s legendary breakthrough year.


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255. Radiohead – “Karma Police” (1997)

On one of the greatest albums ever, one moment always makes my skin crawl, but in the best way possible. The last thirty seconds of “Karma Police” deteriorates into this psychotic melting episode of distorted guitar and leads straight into the terrifying “Fitter Happier.” It recalls the White Album when the “Cry Baby Cry” coda gears you up for “Revolution 9.” It displays the beauty and lasting resonance of album sequencing.


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254. Disco Inferno – “Love Stepping Out” (1992)

Are the experimental rock legends Disco Inferno falling through the cracks? Deerhunter, The Avalanches, and others consider them a huge influence, but their importance and singular aesthetic are rarely discussed among stories of the ’90s. “Love Stepping Out” was the signature hallucinatory track off their groundbreaking ’92 EP Summer’s Last Sound.


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253. A Tribe Called Quest – “Award Tour” (1993)

This is the Tribe’s highest-charting song and the lead single to their third classic in a row Midnight Marauders. The chorus is provided by De La Soul’s Trugoy the Dove.


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252. Fiona Apple – “Sleep to Dream” (1996)

Apple reportedly wrote some of these lyrics when she was 14. If you were looking for where her musical drive was really at, this was the impetus: her against the world with some forceful drums and piano to back her up.


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251. Blur – “Coffee & TV” (1999)

In the standoffish 13, the biggest single is a bit of a respite from the cartoonish experimental rock, but Coxon’s lyrics here still deal with finding normalcy under the strain of alcoholism.


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250. White Town – “Your Woman” (1996)

The Indian-born British Jyoti Moshra was White Town, the small one-man indie pop band that struck gold with this #1 UK hit. The song takes on the perspective of a woman breaking up with a hypocritical Marxist a-hole: a constant struggle for young lovers.


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249. Maxwell – “Ascension (Don’t Ever Wonder)” (1996)

Maxwell peaked with his debut album Maxwell’s Urban Hang Suite, which offered a softer, jazzier Neo soul than his contemporaries. This is music at its most velvety and smooth.


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248. Bob Dylan – “Not Dark Yet” (1997)

Along with “Mississippi” and the week-old “Murder Most Foul,” this Time Out of Mind classic shows Dylan creating a decades-spanning catalog of farewell songs that will match his best work.


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247. Shudder to Think – “X-French Tee Shirt” (1994)

At the same time Jawbox signed to Atlatic Records from Fugazi’s Dischord label, fellow post-hardcore band Shudder to Think also abandoned ship for Epic Records. The resulting album Pony Express Record is an underrated gem of the ’90s with this oddball, winding classic as its centerpiece.


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246. Hole – “Teenage Whore” (1991)

With production from Kim Gordon, Hole’s lead single for their debut album felt like a passing-the-torch moment for indie punk music. The intense underground sound remained, but Courtney Love certainly had more earnest things to say about society.


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245. Built to Spill – “The Plan” (1999)

Keep It Like a Secret is a perfect album, and its opener “The Plan” takes an insane amount of twists and turns across three and a half minutes.


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244. U2 – “Even Better Than the Real Thing” (1991)

Achtung Baby features U2’s most ambitious rock without most of their nagging ego they displayed in the ’80s. “Even Better Than the Real Thing” is the best constructed of their “druggy” mini-epics.


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243. Broadcast – “Echo’s Answer” (1999)

Broadcast’s releases were intermittent and promising in the late-’90s, but The Noise Made by People’s first single at the end of ’99 clarified that Trish Keenan’s muted indietronica project was about to lift off.


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242. Common – “I Used to Love H.E.R.” (1994)

“H.E.R.” in this song refers to “Hip-Hop in its Essence is Real” as Common talks about Hip-Hop losing its way to ego-centric, greedy lyricism. Coming from Common today, this would amount to bougie gatekeeping, but this proved that the 22-year-old upstart had a impactful world view that needed to be heard.


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241. Black Box – “Everybody Everybody” (1990)

Black Box is responsible for one of the most heinous erasures of a woman in music history. The woman you see on the cover is fashion model Katrin Quinol who would merely lip sync in the group’s videos while the real singer Martha Walsh had to eventually sue for credit and royalties. Walsh was dubbed “The Queen of Clubland” with twelve #1 Dance singles to her name, often as a feature and not properly credited.