Top 100 Best Songs of the 1990s (Part One: 100-91)

Since I've already discussed the rules of this list and my honorable mentions, let's get this project underway.

100. "Motownphilly" - Boyz II Men (1991)

When making a list of the one hundred best songs of a decade, one tries to provide an overall picture of the entirety of popular music of said decade. This includes consideration of genres, which, in hindsight, have not held up well at all. The boy-band craze of the late 1990s was one such genre, a reprehensible collection of songs so commercial that one could practically smell plastic emanating from the speakers. While some 90s pop songs demanded the engagement of listeners on both emotional and psychological levels, boy band music demanded nothing more than the virginity of its predominantly tweenage female listeners. Yet, unlike the sexually raw music of the 1950s or the harmonically complex music of the 60s, boy band music of the 1990s dropped any illusions of musical complexity in favor of cheap drum machines, twee vocals, and soulless delivery. Contrary to popular belief, boy band music did not suck because the boys actually didn't play instruments. No, boy band music sucked because whoever was playing the instruments was playing them lifelessly.

Boyz II Men were a breath of fresh air in the toxic atmosphere of the boy band. By far the most vocally talented of the many groups, Boyz II Men were fortunate enough to have soul to back up their studio confections. Their musicianship shines through even on borefests like "End of the Road" and "I'll Make Love to You." By the same token, their lyrics were generally stronger than those of their contemporaries. Compare any of their later songs to the stupidity of songs like the Backstreet Boys' "Everybody (Backstreet's Back)" and LFO's "Summer Girls": the level of maturity is astonishing. Yet Boyz II Men's best song comes from an earlier time, a time of innocence and reminiscence, a time of new jack swing.

"Motownphilly" is a tremendous throwback to the Philly soul records of the 1970s, updated with a uniquely 90s flair. While rock and roll purists object to the overuse of the drum machine, I actually find its precision to be a tremendous asset to the song. Unlike most 90s dance songs, featuring bass drum kicks that are plodding and somewhat monotonous, "Motownphilly"'s studio-created snare provides buoyancy to an otherwise by-the-book soul record. Throw in one of the more effective cowbell lines of the decade, and one has a beat that still holds up. The trumpets pop, the background shouts energize, and the James Brown sample kills.

All these factors considered, the standout element of "Motownphilly" is the vocal. While other new jack swing songs like Bell Biv Devoe's "Poison" end up floudering in their lack of developed melody, Boyz II Men clearly prove their vocal chops here. Using sparing riffs and doo-wop inspired harmonies, the boys make the song sound utterly effortless. All four members of the band get moments to shine, though tenors Wanya Morris and Shawn Stockman end up stealing the show. The two soar through the melody with ease.

The only real flaw I can find in the song is the brief rap breakdown from songwriter Michael Bivins (also of New Edition and Bell Biv Devoe). While it does have a bit of a hype quality to it, it really doesn't end up adding to the song; it just comes across as awkward. Otherwise, "Motownphilly" is simple fun: a new jack swing masterpiece.

99. "Kool Thing" - Sonic Youth (1990)

Maybe it's just my classical ears working overtime, but I've never been able to enjoy Sonic Youth very much. I find a great number of songs from their 80s opuses, Sister and Daydream Nation, nigh unlistenable due to the overuse of feedback. Nor do I find their constant shifts between angst and counter-angst particularly compelling. Other times, their songs leave no impact whatsoever. I still can't muster up any emotion whatsoever for "100%" in spite of it being called Sonic Youth's best 90s song. At the same time, to ignore the band's artistic legacy in the canon of alternative rock, the 90s most dominant music scene, would be outright disingenuous. 

"Kool Thing," Sonic Youth's strongest song (in my opinion), thus languishes towards the bottom of this list. That's not meant to be an insult: it was good enough to actually make the list. It's just that "Kool Thing" isn't as timeless a classic as the songs in the top fifty. It's a very good alternative rock song as opposed to an absolute must-own, must-adore, game-changing alternative rock hit. That being said, "Kool Thing" is at once Sonic Youth's most approachable yet most intense song. The dual guitars of Thurston Moore and Lee Ranaldo shine in perhaps the most spectral guitar riff of the 90s, creating an atmosphere of terror and chaos. Yet, unlike most Sonic Youth songs, this mania is centered in a solid musical idea and motif. The song has a clear structure that provides cohesion as opposed to confusion.

Lyrically, "Kool Thing" is a seeming adoration of 1960s radicalism, particularly the extremist tendencies of the Black Panthers. While more conservative members of society might find this song shameful for promoting such a controversial political group, they might find some consolation in Kim Gordon's subdued and caustic delivery. There's a clear implication that the Black Panther Kool Thing of the title is more bark than bite, as illustrated by one of the most bizarre cameos in alt rock history. Chuck D, the emcee of Public Enemy (AKA the greatest hip-hop group in history), appears and half-heartedly mouths off some alterations on his song titles. Is this supposed to be a subversion of the "black power" anthems that motivate the music of Public Enemy and the politics of the Black Panthers? Sonic Youth makes the right choice and permits the listener to be the judge.

"Kool Thing" combines spectral guitars, sexual innuendo, and sixties radicalism to produce one of the more memorable alternative rock tracks of the 90s. It's a bit lacking in finesse and a bit on the nose, keeping it from getting any higher, but, as it is, it's a strong song.

98. "Via Chicago" - Wilco (1999)

My listening experiences with Wilco have been... varied. Like most, I initially became familiar with the group through their 2002 release, Yankee Hotel Foxtrot, but the record didn't really leave an impression. Listening to their 90s catalogue, however, I've become a bit more interested in the band. The songs I heard in researching for this list were all quite nice, and they encouraged me to take a listen to more of Wilco's 2000s work, including a re-evaluation of Yankee Hotel Foxtrot. That being said, I think the strongest 90s song from the band is "Via Chicago," the emotional centerpiece of the Summerteeth album. The gentle guitar strums belie the biting sense of self-loathing that permeates throughout the entire song. And though such self-loathing would serve to diminish a song by a lesser band, Wilco treats the subject with enough finesse to land them a place on the list.

While the opening lines, "I dreamed about killing you again last night / it felt all right to me," might raise more than a few eyebrows, there's enough ambiguity throughout the rest of the song to make the line work. It is possible to interpret "Via Chicago" as either the aftermath of a tumultuous relationship or the rejection of long-held dreams in favor of a return to one's roots. Though the rest of the song's imagery is somewhat abstruse, "Via Chicago" manages to avoid most assertions of pretension through unabashed pathos. Jeff Tweedy's voice is just thin enough to provide vulnerability while strong enough to show the strength of his convictions.

The instrumentation of "Via Chicago" is also incredibly rich. The subtle use of the banjo combined with the prominent use of guitar feedback and backwards violins creates an atmosphere of discomfort that perfectly represents the song's profound sense of anxiety. The harmony occupies a comfortable third throughout, occasionally enhanced by vocal doubling on the most important phrases. There are so many subtle touches on "Via Chicago" that each listen reveals a little bit more.

If it has all these positive qualities, why is "Via Chicago" so low? On the one hand, there are plenty of other 90s songs that I think have even more to offer. On another hand, "Via Chicago" shares a frightening amount of musical similarity to Neil Young's masterpiece song, "After the Goldrush" (quite possibly Neil Young's best). While "Via Chicago" seems to expand upon the ideas of "After the Goldrush," the similarities are a bit too on the nose for me to put "Via Chicago" any higher. At any rate, though, both songs are worth a listen.

97. "Gonna Make You Sweat" - C+C Music Factory (1990)

Embarrassing choice? Perhaps. But I hold that "Gonna Make You Sweat" was the most popular and enduring of the 90s dance singles, if not necessarily the best or most innovative. Additionally, it's the only 90s dance song that's managed to survive in the popular consciousness almost untainted by major criticism. Sure, the rap breakdown is somewhat silly, but the rest of the song is pure dance music bliss. Furthermore, it's quite refreshing to hear a dance song that is actually danceable, as compared to most of the post-Discovery autotune, EDM-inspired, lifeless shlock we've been listening to for the past fifteen years.

The beat to "Gonna Make You Sweat" is nothing less than masterful. The guitar takes Survivor's "Eye of the Tiger" and turns it into a danceable groove. The drum fills are entertaining and energetic. Indeed, the entire rhythm section is incredibly tight. The horns are studio-generated, but they suit their purpose well enough. Even the reverb is effective. "Gonna Make You Sweat" is essentially the best elements of 80s hair metal combined with Madonna's "Vogue."

But the real secret to "Gonna Make You Sweat"'s effectiveness is Martha Walsh, the singer of the immortal line: "everybody dance now." Walsh was originally the lead singer of the notable one-hit-wonder, the Weather Girls, of "It's Raining Men" fame. Throughout the 80s and 90s, Martha Walsh provided vocal hooks for a variety of dance hits, including honorable mention "Everybody Everybody" by Black Box. As awesome as her vocals are, the record company refused to include her in the music video, instead putting her vocals in the mouth of C+C Music Factory member Zelma Davis, a legally and morally suspect action considering the weight difference between Walsh and Davis. Fortunately, Martha Walsh managed to sue the label and earn denied royalties; it is very much thanks to Walsh that featured vocalists are now credited on songs.

Sadly, "Gonna Make You Sweat" is little more than a joke nowadays, used to trigger a dance sequence in low-grade comedies. It's a shame. "Gonna Make You Sweat" was the song that put dance music back onto the pop charts, an act which wasn't inherently awful in and of itself. After Lisa Lisa and the Cult Jam did their best to destroy the genre, we desperately needed a song like "Gonna Make You Sweat" to save it. Other dance songs from other subgenres might be more musically interesting and higher on this list, but this song is the one to credit for the genre's enduring popularity.

96. "The Choice Is Yours (Revisited)" - Black Sheep (1991)

I hesitate to call myself a rap "fan," as I spend little time investigating underground hip hop LPs and EPs. However, I have a tremendous respect for the art form, and I recognize that most of the best music of the past 25 years comes from the genre. In the 1990s, hip hop entered its golden age, with many of the genre's seminal albums being released to a public now willing to buy records from what was originally a niche genre. Yet hip hop lost little of its luster as it entered the mainstream. It instead diversified, with some rappers taking a more happy-go-lucky approach to the genre, some darkening their subject matter to create the threatening "gangster rap" scene, some incorporating West Side cool, some incorporating East Side savagery, some embracing absurdity, some embracing sheer sonic terror. There was so much good rap music in the 90s that hip hop takes up an entire quarter of this list, and that's not including off-shoot genres such as trip hop. Rap in the 90s deserved its dominance.

Black Sheep's "The Choice Is Yours (Revisited)" is the lowest ranked rap song on the list, mostly due to its overall "goodness" as opposed to overall "greatness." While a good rap song with some solid verses, it's managed to endure by virtue of its memorable chorus as opposed to its considerable lyricism. The simple declaration of "you can go with this or you can go with that" has been remixed countless times, perhaps most memorably by Fatboy Slim in the song, "Weapon of Choice" (complete with its music video starring Christopher Walken). Yet it's quite interesting to consider where this infamous phrase comes from. "The Choice Is Yours (Revisited)" was released just as gangster rap was starting to make gains in the hip hop community. Black Sheep essentially poses the question to the youth listening to the song: are you going to side with violence and drugs, or are you going to side with personal freedom and societally respectable happiness?

But the subtler touches of "The Choice Is Yours (Revisited)" make it a far better song than its oft-sampled chorus would have one think. Chief emcee Dres has a flow that is wholly musical and engaging, varying up his style with syncopations that make each word pop. He skirts around all of the hip hop conventions while also subverting them, including mocking the then recent trend of rappers spelling out their names before beginning rap verses. He even writes raps that demonstrate respect for women; what a shock!

It might not have been the most innovative hip hop single of the 90s, but "The Choice Is Yours (Revisited)" is a memorable and solidly written hip hop song that has stood the test of time. It's not overly complex, but there's enough skill and dexterity at work here for me to wholeheartedly endorse it.

95. "Mouth Breather" - The Jesus Lizard (1991)

Though Fugazi was the most critically respected of the 90s hardcore punk groups, they never released a song quite as good as The Jesus Lizard's hypnotic "Mouth Breather." The Jesus Lizard is as raw a band as has ever existed, and "Mouth Breather" is the epitome of their guitar and drum savagery. The song is a wall of sound that is at once imposing and alluring, gradually lulling the listener into a sense of security with its spiraling guitar riff, right before assaulting the listener with a horrifying vocal. While grindcore bands perform a similar balancing act with amusical and nigh unlistenable results, the Jesus Lizard walks the fine line between noise and music perfectly.

The musical structure of The Jesus Lizard is a single riff, spanning a distance of no more than three triads. The song then applies a descending harmonic sequence, just as the song's lyrics grow more twisted and violent. Duane Denison's guitar groove is absolutely infectious. Even better is the drumming from Mac McNeilly; his fills tear the song to pieces. And David Yow's voice, while as amusical as is typical for hardcore punk, really boosts the song's terrifying aesthetic. I can only resist head-banging to this tune because the tune is written in 2/4 time, a rarity for both punk music and rock music.

Lyrically, "Mouth Breather" seems to simply be a condemnation of a friend for his "mouth breather" qualities - offering a sense of Seinfeld-ian humor. Ye at the very end of the song emerges a twist so dark as to turn "Mouth Breather" into one of the great murder ballads of the 1990s. We soon realize just why the guitar riff is so dark and why the song is written in a minor key. "Mouth Breather" might be a fun song on its own, but it leaves the listener feeling the perfect level of discomfort upon its ending.

On the whole, "Mouth Breather" is an excellent introduction to the world of hardcore punk. It's got just enough noise, just enough wit, and just enough groove to get anyone interested. How far down the rabbit hole you choose to go... I'll leave that for you to decide.

94. "The Man Don't Give a F***" - Super Furry Animals (1996)

Never before has swearing been so fun. "The Man Don't Give a F***" drops the F-bomb more than 50 times in the span of four minutes. However, the song is so delightfully funky that the listener can't help but sing along. The song is so over the top in its profanity that the swearing essentially becomes meaningless. Indeed, the word practically becomes humorous as it is incorporated into nearly every melodic line of the song. "The Man Don't Give a F***" isn't particularly deep, but its sheer audacity pushes it to a far more profound commentary on the nature of censorship than the Super Furry Animals could have ever intended.

As for the Super Furry Animals themselves, they were perhaps the most undefinable Britpop act of the 90s. Not fitting neatly into one sound of Britpop or another, they lent themselves to radical musical experimentation. I nearly included "Ice Hockey Hair" on this list, if only for its excellent sound production. However, I ended up grooving to "The Man Don't Give a F***" much more: the cards are as they fell.

Lamentably for the song's placement on this list, "The Man Don't Give a F***" centers its entire structure upon a single sample of Steely Dan's "Show Biz Kids," one of the more standard songs in the Steely Dan catalogue. However, Steely Dan member Donald Fagen objected to the sample so much that he received 95% of the royalties before he permitted the song to be released as a single. If that isn't an example of greed at its highest degree, I don't know what is; it's as if Donald Fagen is the taxman of the Beatles' "Taxman." (Actually, the percentages line up exactly.) While I understand that any artist should be paid for this level of sampling, the transformative use in this case certainly warranted significantly less royalties. The song manages to take a simple, monotonous phrase and restructure the entire harmonic rhythm to transform it into a rallying cry. This is a model of how good sampling is done.

"The Man Don't Give a F***" is the most joyfully crass pop song of the 1990s, even if it didn't sell particularly well in the United States. Fortunately, the Internet has enabled us music fans to learn more about songs this joyously stupid from the other side of the Atlantic. It might be simple, but I don't give a f***. It's a grade A pop song in my book.

93. "Plush" - Stone Temple Pilots (1992)

The Stone Temple Pilots have received more than their fair share of criticism. Most of the hatred centers on lead singer Scott Weiland, whose shtick of ripping off Pearl Jam lead singer, Eddie Vedder's, vocal style did not go over very well. Weiland certainly didn't help critics' perception of him through his multiple drug busts and controversies, as well as his being a general a**hole during interviews and concerts. Contemporary music critics tore the band to pieces, calling them out for plagiarizing others' sound and their often morally suspect lyrics ("Sex Type Thing," anyone?). Nowadays, however, the Stone Temple Pilots' reputation has improved drastically, with Purple being considered one of the best records of 1994, the most highly regarded year of the decade. While my initial fandom of STP has mellowed with age, I cannot deny two of their songs a place in the 90s canon: "Interstate Love Song" and "Plush." The two are very similar, stylistically, so one had to miss the cut. Since I like both equally, I defaulted to the song that received the most accolades. "Plush" has a Grammy; "Interstate Love Song" does not.

I'll be blunt: the lyrics to "Plush" are pretty terrible. The writing of "when the dogs begin to smell her/will she smell alone?" is downright cringe-worthy. But I'm not wholly opposed to songs that use words to convey an aesthetic rather than a story. (Granted, songs that do both are usually better, but I digress.) In "Plush"'s case, the technique works well enough. The sludgy guitar combined with the low-brow imagery creates a depressing mood that evokes 90s grunge perfectly. Also, if I look at the lyrics with my head upside down and backwards, I can see the semblance of a relationship falling to pieces. The idea is not articulated very well, but something is at work.

Scott Weiland's vocals are one of the strongest elements on the track. As the critics have noted, there are more than a few moments in which he sounds like Eddie Vedder. Indeed, on the pre-chorus, he seems to sing the vocal line of Pearl Jam's "Even Flow." Yet Weiland channels a more soulful sound than Vedder, relying more on the moroseness of vocalists like Layne Staley and Kurt Cobain as opposed to the pure rage found in Eddie Vedder and Chris Cornell. I also appreciate the use of flatted pitches to make the vocal sentiment more concerned. Purer singers like Vedder and Cornell would not work as effectively with this material.

Yet the absolute best part of "Plush" is the guitar. The tone is grunge perfection, with a combination of wah-wah and flange as to give each note a bubbling quality. There are also many different styles of play at work, from power chords to dreamy arpeggios. "Plush" could have been a relatively small song considering the size of the Stone Temple Pilots, but it feels huge. Dean DeLeo milks each chord for what it is worth, pronouncing each shift just the right amount to give the song a real sense of momentum. "Plush"'s drums are somewhat plodding, but the guitar manipulates that thudding beat so to give the song a real drive. As the song builds ever so slightly by the final chorus, the release is cathartic.

"Plush" might not be the most graceful or meaningful of the grunge songs released in the 90s, but it's one of those songs that just typifies the genre. The song serves to represent the bulk of 90s grunge, which is remarkably absent from the lower half of the list. The higher quality grunge songs occupy far more prestigious placements.

92. "Miss Misery" - Elliott Smith (1997)

The early death of Elliott Smith will forever be considered one of the great tragedies of indie rock. Over the course of six studio albums, he managed to write several of the most genuinely enjoyable and introspective songs the scene has ever heard. "Needle in the Hay," "Between the Bars," and "Waltz #2" were all strong contenders for the list, but I ultimately sided with Smith's most "popular" song: "Miss Misery." I use the term "popular" lightly here, as "Miss Misery" is one of the less respected songs in the Elliott Smith canon amongst indie fans. Ever since Gus Van Zant used the song in Good Will Hunting, there's been a bit of a backlash against the song. However, seeing as practically all of Elliot Smith's songs are great in some way, I am more than willing to accept this backlash as hipster posturing. "Miss Misery" is a superb piece of songwriting craft that should not go under-recognized.

"Miss Misery" is one of the strongest break-up songs in a decade filled with break-up songs. "Next door the TV's flashing/Blue frames on the wall/It's a comedy/Of errors, you see/It's about taking a fall": even while relating such detail, Smith manages to add internal rhyme to his verses. Most of the song's lyrics, such as these, are loaded with observational detail. However, unlike many lesser indie artists, Smith never resorts to shameless apophenia in order to make his point. His details, while occasionally Joycean in their presentation, clearly do have a rhyme and reason related by the syntax and metrical structure. The lyrics are pointed and poignant, leaving the listener wholly satisfied.

"Miss Misery" also manages to remain interesting in the musical department as well. While many of Smith's songs are stripped down acoustic guitar pieces, he does not hesitate to incorporate George Harrison-toned guitar and piano. "Miss Misery" also has two bridges, both of which have different chord structures: a striking deviation from the majority of indie rock songs. Another nice addition is the doubled vocal and subtle harmonies. It's surprising how effective a simple major third can be to enhancing a song's sound.

It might not be the most depressing song in the Elliott Smith catalogue, but "Miss Misery" is heartbreaking in its own way and effective on nearly every level. It would be higher on the list if it weren't for a lack of overall influence on the genre. Most other indie songwriters flocked towards the more depressing, less produced songs on Smith's albums. Not to discredit those songs in any way, but "Miss Misery" is so good it got nominated for an Oscar.

Granted, it lost that Oscar to Celine Dion... but let's not talk about that.

91. "Friends in Low Places" - Garth Brooks (1990)

Before the 90s alternative fans and country music purists throw temper tantrums in the comment section, hear me out. To understand the placement of "Friends in Low Places" on this list, one has to understand the state of country music when this song was released. After its commercial heyday in the 1970s, country music struggled to keep hold of its niche during the 80s. Unfortunately, the AM radio which it had been so able to dominate over the past forty years was gradually phasing out country music in favor of talk radio. Even worse, the only country music it was playing was the classics: Johnny Cash, Hank Williams, Patsy Cline, etc. George Strait and most other country musicians still producing new music were running into serious trouble. "Friends in Low Places" changed all of this almost single-handedly.

Garth Brooks found a new home for country music on FM radio stations, releasing "Friends in Low Places" to a much larger audience than what would be heard by the traditional country market. Now, it wasn't just Americans listening to country; it was the entire world. "Friends in Low Places" turned Garth Brooks and country music into a global phenomenon, ushering in what is known as the fifth generation of country music. Granted, many of the byproducts of this fifth generation have taken country away from its roots, giving many good reason to complain, but the actual change secured country music's survival. In terms of influence alone, I'm not sure there's a single song from the 1990s that so shaped popular music's development than "Friends in Low Places."

Remember: all of that information is extraneous to the quality of "Friends in Low Places," which I would argue is still one of the best country songs released in the past 25 years. From the chorus alone, it would seem like "Friends in Low Places" is an average drinking song, but the verses tell a completely different story. While the narrator might have his "friends in low places," his friends certainly don't put him in a good place. He's clearly drinking to drown his sorrows, but his drinking only manages to make him feel good temporarily. Even worse, it manages to further jeopardize his relationships with others. He practically ruins his ex-lover's wedding with his drunken antics and is thrown out of the party completely. Needless to say, this song contains the right amount of irony to wholly redeem any of its lackadaisical elements.

Best of all, the music of "Friends in Low Places" contains all of the fireside fun of Johnny Cash and Hank Williams classics without dipping into the stupidity into which so many fifth-generation country songs fall. Though it is a simple joke, the melodic articulation of "low" never fails to draw a light chuckle. After all, if the Sherman Brothers could get away with the same type of humor in "Spoonful of Sugar," why can't Garth Brooks? The guitar solos are pleasant, as is Garth Brooks's voice. The final chorus is as spirited as any good country song should be. It's a fun song. Period.

Indeed, "Friends in Low Places" is such a good country song that its shadow looms over the entire fifth generation of country music. Brad Paisley's "Alcohol," widely considered to be one of the best country songs of the 2000s, is little more than a slight expansion upon "Friends in Low Places" - right down to the theme and the chord structure. "Friends in Low Places" is the only fifth generation country song even mildly respected by country music aficionados, such as the Houston Press's William Michael Smith. Sadly, lesser artists attempting to capitalize on "Friends in Low Places"'s worldwide success have managed to slowly drag country music into a perilous hole. We can only hope a song this good can manage to save it.