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160. Neutral Milk Hotel – “In the Aeroplane over the Sea” (1998)

Jeff Mangum’s earnestness and odd Anne Frank obsession has been the subject of debate for over twenty years, but no matter how you feel about the whole album, the last verse of this song will simply gut you if you let it: “How strange it is to be anything at all.”


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159. James – “Laid” (1993)

James is a band featuring no people named James. They were on their fifth album when they first worked with Brian Eno and the resulting title track became a big hit on US college rock stations.


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158. The Notorious B.I.G. – “Things Done Changed” (1994)

The beat is a combination of samples from Biz Markie, Dr. Dre, and ’70s soul group The Main Ingredient, but the main draw is one of the hardest deliveries from Christopher Wallace on the first song track from Ready to Die.


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157. Stardust – “Music Sounds Better With You” (1998)

Thomas Bangalter and Alan Braxe would be involved in the greatest dance music of the 21st century, but in 1998 with vocalist Benjamin Diamond, they made one song that was an immediate global hit. Chaka Khan’s “Fate” is sampled and looped to create the disco pop classic. They’ve never worked together again.


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156. Kelis – “Caught Out There” (1999)

Before she brought all the boys to the yard, she was screaming “I HATE YOU SO MUCH RIGHT NOW!” into a megaphone. The Neptunes-produced track wasn’t the massive hit it was supposed to be, but it’s a classic receiving the sample treatment from artists like James Blake for “CMYK.”


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155. Dinosaur Jr. – “Start Choppin” (1993)

Along with “Freak Scene,” this is the best example of Dinosaur Jr.’s pop rock allure. J Mascis wasn’t a strong singer — or even that much of a lyricist — but his slacker croak carried a lot of personality and emotion.


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154. Portishead – “Glory Box” (1994)

Beth Gibbons’ vocal work on Dummy brought a feminine retro soul aesthetic to the heavily-masculine world of industrial trip hop. “Glory Box” is the signature song of Portishead’s whole discography.


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153. Ol’ Dirty Bastard – “Shimmy Shimmy Ya” (1995)

Ol’ Dirty Bastard had a pop sensibility that the Wu-Tang solo discography often lacks. He could let a killer beat play out and repeat hooks and verses to make them more memorable, but he would still throw in oddball choices like playing a verse backwards. As rap incorporated more pop elements in the 21st century, ODB was the Wu-Tang member artists looked to for inspiration.


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152. DJ Shadow – “Building Steam With a Grain of Salt” (1996)

Never released as a single, the first song track off Endtroducing… has nonetheless become one of instrumental hip hop’s go-to tracks. The song is pretty standard until the 3-minute mark when the drums go haywire and more dreamy elements enter the mix.


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151. Arthur Russell – “This Is How We Walk on the Moon” (1994)

Arthur Russell made one solo studio album in his lifetime — the classic World of Echo. After that album, Russell was diagnosed with HIV and later died in 1992. He left behind a wealth of unreleased material that has surfaced into multiple posthumous classics. The first of these was Another Thought which collected much of what he was working on in the voice-and-cello style. “This Is How We Walk on the Moon” came from before World of Echo and was maybe a little too pop to be worked in; the last two minutes features an exuberant horn section that only Russell could envision.


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150. Spacehog – “In the Meantime” (1995)

Spacehog brought some necessary glam into hard rock in the mid-’90s. Frontman Royston Langdon sung in a proudly-indecipherable accent and would posture in the music video with a “yeah, I made this” vibe.


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149. Christina Aguilera – “Genie in a Bottle” (1999)

Aguilera was introduced to the pop charts with this suggestive single that is still her best song to-date. The production from ’80s legends Kipner and Frank is some of the best from pop’s critical resurgence around this time.


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148. Oasis – “Champagne Supernova” (1995)

Why does anyone play “Wonderwall” when this is on the same album? The Morning Glory closer best sums up Oasis’ massive success and the inspiration of their narrative of a couple boys from Manchester playing to the biggest crowds in UK history.


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147. Harvey Danger – “Flagpole Sitta” (1997)

Though just a one-hit wonder, Harvey Danger took the alternative power pop of Green Day and Weezer towards something a little more emo, anti-Grunge, and knowingly sardonic with this manic classic.


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146. Len – “Steal My Sunshine” (1999)

With a spiritual ancestor of the Human League’s “Don’t You Want Me,” this indie pop single broke through as a top-ten hit. The kaleidoscopic rave music culture that started the ’90s came full circle with this perpetual song of the summer candidate.


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145. Cutty Ranks – “Limb by Limb” (1993)

Cutty Ranks was insanely prolific in the ’90s with over 80 singles over the decade. “Limb by Limb” is the most popular of the bunch. From the borderline-techno beat to his forceful delivery, “Limb by Limb” is the greatest example of Dancehall in the ’90s.


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144. The Beta Band – “Dry the Rain” (1997)

What a song to open your career with: a 6-minute indie folk classic that would be the subject of a High Fidelity in-movie promotion from Cusack. It has become an anthem of the upbeat horn-laden indie rock scene of the late-’90s.


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143. Basement Jaxx – “Red Alert” (1999)

With the lead single to their debut album, Basement Jaxx crafted a digitized P-Funk vibe for something a little more dynamic than the Big Beat scene but way more danceable than IDM.


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142. Dr. Dre – “Fuck Wit Dre Day (And Everybody’s Celebratin’)” (1992)

In the dissolution of N.W.A., Dr. Dre felt wronged by Jerry Heller and Eazy-E based on complicated contract disputes that inevitably involved the king of drama Suge Knight. The split was anything but amicable, and it resulted in one of the biggest diss songs ever on the Billboard charts.


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141. Pet Shop Boys – “Being Boring” (1990)

“Being Boring” was one of the least successful Pet Shop Boys’ singles at their peak, but it’s grown as a fan favorite for its sophisti-pop beauty and reflective melancholy.


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140. Nirvana – “All Apologies” (1993)

Despite its straightforward structure, the In Utero closer is heavy. It has taken on the role of representing Cobain’s last pain-stricken days ending with a repetition of the egalitarian Buddhist quote “All in all is all we are.”


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139. Sleater-Kinney – “Get Up” (1999)

Like much of Sleater-Kinney’s best work, “Get Up” remains underappreciated. The guitar-drum interplay here was the best going at the time, and Corrin Tucker’s lyrics are surrealist in a way that they are never given credit for. It’s an impeccable, weird rock song.


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138. Belle & Sebastian – “Get Me Away from Here, I’m Dying” (1996)

The best standalone song on If You’re Feeling Sinister is the perfect meeting place of childlike melodies and lyrics examining deep artistic anxiety that hadn’t really been explored before.


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137. Raekwon (ft. Ghostface Killah, Method Man, & Cappadonna) – “Ice Cream” (1995)

“Ice Cream” is one of the best non-Wu-Tang Wu-Tang songs of the ’90s; the two best rappers of the bunch (Ghostface and Raekwon) offer killer verses, and Method Man acts as the hypeman bringing the hook.


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136. The Cranberries – “Linger” (1993)

Dreamier than “Zombie” and easier to emotionally sing along with than “Dreams,” this is the best Cranberries single. “Linger” was completely rewritten by Dolores O’Riordan when she entered the band as the new lead singer. She leans into her Irish accent for her unique stamp on the song’s chorus.


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135. Fatboy Slim – “Praise You” (1998)

Norman Cook reached #1 on the UK charts with three different acts: “Caravan of Love” by the Housemartians, “Dub Be Good to Me” by Beats International, and then this under his most famous alias. The song is a mix of a Chicago gospel sample by Camille Yarbrough, a 1970s Disney disco version of “It’s a Small World,” and a test piano sample by JBL. Big Beat peaked here.


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134. Souls of Mischief – “93 ’til Infinity” (1993)

Souls of Mischief tend to be lost in the wealth of great rap music around this time, but 93 ‘Til Infinity is a steady front-to-back classic with its title track being a laid back party starter.


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133. Sade – “No Ordinary Love” (1992)

Sade only released one album in the ’90s, and it’s as much a classic as their first three from the ’80s. Love Deluxe and lead single “Ordinary Love” finds the band’s Latin jazz roots updated with some trip-hop style drum machines.


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132. OutKast – “Elevators (Me & You)” (1996)

From its alien cover to the minimalist, echo-y production to the deadpan-yet-braggadocious hook, “Elevators (Me & You)” is one of the strangest major rap releases to this day. Oddly enough, this was OutKast’s biggest hit of the ’90s; rewriting pop standards would be an OutKast standard.


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131. UGK – “One Day” (1996)

Ridin’ Dirty had no singles or music videos released, but there’s no dispute it’s a nominee for the greatest Southern hip-hop album of all time. Ronnie Spencer interpolates an Isley Brothers’ classic to set the mood for Bun B and Pimp C to speak to the morbid anxieties surrounding their lives and in the broader culture.