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The 500 Greatest Songs of the 1990s – 30 to 21

30. “I Try,” Macy Gray. Songwriters: Macy Gray, Jeremy Ruzumna, Jinsoo Lim, David Wilder; #5 pop; 1999. Macy Gray’s 1999 album “On How Life Is” went triple platinum, pushed to those heights by the neo-soul heartbreak, quiet storm of “I Try.” A torch song about being torched, if you will, and a perfect fit for Gray’s smokey/raspy voice. Part of the power of the song is the expression of the physical impact of the emotional pain – not just crying and dreaming, but choking and stumbling. The lost love has the singer wrecked in every conceivable way. Gray, “Back when we made it, I didn’t really get why people were so into it – I was pleased by its success, but I didn’t really understand the reasons. Now, I understand – it sounds like nothing else that was around at that time.”

29. “Jagged,” Old 97s, Songwriters: Rhett Miller, Ken Bethea, Murry Hammond, Philip Peeples; Did Not Chart; 1999. “Jagged” sounds like a man at the end of his rope, both Ken Bethea’s fuzzed out guitar and Rhett Miller’s raspy, exasperated vocals convey that the narrator is fighting a losing battle. Rock critic Jim Connelly, “(Rhett Miller has) probably never better than on the chorus of ‘Jagged,’ where he’s so off-kilter that he’s slipping into a near-falsetto at the end of every single one of those choruses, as if to say that his jaggedness is even affecting his vocal control.” Keith Phillips of the A.V. Club on the band’s songwriting skills, “(The) Old 97’s seem to have perfected the art of crafting songs that dare listeners not to sing along.” Really weird fact – “Jagged” was penned for, but not used in, a Vince Vaughn movie. Miller, “Sometimes writing a song is straight-up commerce.”

28. “Love Sick,” Bob Dylan. Songwriter: Bob Dylan; Did Not Chart; 1997. Bob Dylan experiences the type of love that destroys a man’s soul on “Love Sick,” the lead track on the 1997 Grammy Award winning album “Time Out of Mind.” Producer Daniel Lanois, “We had quite a crew in there including Augie Meyers on organ from Texas. He’s a specialist in that little back beat skank organ I call it. That little stab at the beginning came from Augie and the more celestial sound came from Jim Dickinson on a Wurlitzer and that provided all that mystery and cascading of sounds. And then we had two of the greatest drummers in the world, Brian Blade and Jim Keltner. As subtle as the drums may be on that record there’s a lot of southern feeling on that record.” As for Dylan, he notes that the streets are dead, the clouds are weeping, and his lover has destroyed him with a smile. He sounds like he’s married to despair with no hope of annulment.

27. “Bad Reputation,” Freedy Johnston. Songwriter: Freedy Johnston; #54 pop; 1994. Freedy Johnston had the biggest commercial push of his career with the Butch Vig produced single “Bad Reputation,” which almost reached the pop Top 40. It’s easy to see why it didn’t, because the theme is a little too complicated for commercial radio. “Bad Reputation” is about a man desperately in love (“Do you want me now?/Do you want me now?”), but with too much pride to become a better person for his potential lover (“Don’t try to be an inspiration/Just wasting your time, time, time”). The narrator is emotionally stuck between his stubbornness (“Nobody’s gonna tell me who to love”) and his weaknesses (“I couldn’t have one conversation/If it wasn’t for the lies, lies, lies”), that ends with him “breaking down, down, down.” From the website The Second Single, “The song is gorgeous, beginning with Johnston’s vocals and acoustic guitar before giving way to a full scale ballad, complete with guitars so jangly, The Byrds may have asked him to ease off on the treble.” Johnston, “We were almost at the end of making ‘This Perfect World,’ and Butch Vig asked if I had any more songs. I told him I had this one song that was called (at the time) ‘Talk, Talk, Talk,’ but I didn’t like it too much. He heard it and said, ‘That’s going on the album.’ I learned something from that (laughing). If I write something that annoys me, I need to play it for someone else.”

26. “Better Man,” Pearl Jam. Songwriter: Eddie Vedder; #13 pop; 1994. Eddie Vedder penned this song about settling for less and/or being in an abusive relationship when he was a teenager and once said, “It’s dedicated to the bastard that married my momma.” Melodically, “Better Man” has elements of The English Beat’s “Save it for Later,” but has a much more powerful emotional depth. Matt Popkin of American Songwriter, “The verbal cadence of the opening verse sounds like a nursery rhyme with its short bursts of information – ‘Waitin’/Watching the clock/It’s four o’clock/It’s got to stop.’ The guitar sounds so hesitant to even play; the organ brews right under the surface. And then the song releases all that tension: the drums enter; Vedder sings chorus, ‘She lies and says she still loves him/Can’t find a better man.’ And you believe him. How could you not?” According to producer Brendan O’Brien, it took several recordings before Vedder and his grunge colleagues were comfortable with “Better Man” because “it was such a blatantly great pop song.”

25. “The Road Goes on Forever,” Joe Ely. Songwriter: Robert Earl Keen; Did Not Chart; 1992. Joe Ely alternated between releases on MCA Records and independent labels during the 1990s and had his most mainstream country contemporary production on the 1992 “Love and Danger” album, courtesy of Nashville bigwig Tony Brown. Ely cut the definitive version of Robert Earl Keen’s “The Road Goes on Forever” for that album, a story song about two small town losers (a slutty waitress and a small time pot dealer) who hit the road for an adventure that went awry. The scorecard at the end of the tune – one dead cop, one man on death row, and a lady with a new Mercedes Benz. Songwriter Robert Earl Keen, “The Sonny and Sherry characters are based on real characters that just couldn’t stay out of trouble. No matter what happened, no matter what fortune fell on them, they would screw that up. That’s where it started from.” This violent tale has been covered by Jack Ingram, the Highwaymen, and namechecked in Todd Snider’s “Beer Run,” perhaps as validation that the party never ends.

24. “My Life,” Iris Dement. Songwriter: Iris Dement; Did Not Chart; 1994. Iris Dement was signed to Warner Brothers Records for her 1994 Nashville recorded “My Life” album. However, the label was smart enough not to try to put her unique talent in the Music City assembly line production mode; she continued to deliver her country/gospel sound with serious emotional themes. The title track is as moving a song as you will ever hear – Dement notes the relative insignificance of an individual human life as compared to the scope and history of the universe. Then, she discovers her own self worth, not in the approval of a higher power, but in giving her mother joy, making her lover smile, and providing comfort to friends when they are hurting. Iris concludes that she “can make it seem better for a while” and it sounds like mankind’s noblest gift.

23. “Mind Playing Tricks on Me,” Geto Boys. Songwriters: Brad Jordan, Doug King, William Dennis; #23 pop/#10 R&B; 1991. Early 1990s rap music was about projecting strength, not vulnerability, but the Geto Boys were sharing their demons about receiving street retribution on their 1991 pop hit “Mind Playing Tricks on Me.” The sample of “Hung Up By My Baby” from Isaac Hayes, written for a 1974 blaxploitation film, serves as the perfect cinematic backing to the lyrics about drug deals, street beat downs, and the weight of bad karma. The fact that Geto Boys rapper Bushwack Bill had shot an eye out in a domestic dispute less than two weeks before the single was released added to the aura of danger surrounding the group. Rodney Carmichael of NPR, “This was confessional rap — street ministry. Scarface (rapper Brad Jordan) was acknowledging emotions a generation of black boys had been conditioned to hide.” Brad Jordan, perhaps describing how his worldview informed his music, “When you live in a society that repeatedly tells you that it values a white person’s life, safety, values, and lifestyle more than your own, and you get reminders of it every day and at every turn…it’s very easy to come to the conclusion that the best solution to all of this shit is violence.”

22. “Mary Jane’s Last Dance,” Tom Petty and the Heartbreakers. Songwriter: Tom Petty; #14 pop; 1993. The grunge crowd had pretty much eliminated classic rock from the pop airwaves by 1993, but Tom Petty and the Heartbreakers had their penultimate Top 40 single with the “oh my my, oh hell yes” groove number “Mary’s Jane’s Last Dance.” Petty did some first rate recycling here, merging “Waiting for the Sun” by the Jayhawks with a riff from Cheap Trick’s “The Ballad of T.V. Violence (I’m Not the Only Boy).” Matthew Greenwald of All Music on another influence, “The simple, three-chord pattern is disarmingly similar to Neil Young/CSN&Y’s ‘Ohio,’ and the rising, modulating chorus is also reminiscent of that classic. However, lyrically, Petty takes the song in a different direction, utilizing his ability as a storyteller to create an autobiographical tale through romance and the artistic process.” Drummer Stan Lynch on his last recording with the band, “I was told (by Rick Rubin) that the drums should sound like ‘Gimme Shelter’ and he only wanted to hear one fill. First off, I’m going, ‘Who the fuck are you anyway? You seem like a cool guy. You seem to be successful, and that’s great. But I don’t really give a shit about you. You’re a hired gun. There’s five guys here that matter, and you ain’t one of them.’”

21. “Flagpole Sitta,” Harvey Danger. Songwriters: Sean Nelson, Jeff J. Lin, Aaron Huffman, Evan Sult; #31 pop; 1997. Harvey Danger’s not sick/not well pop punk masterpiece “Flagpole Sitta” is one of the most sarcastic singles to ever hit the Top 40. It’s a mixture of self-gratification, self-deprecation, and a look at a culture that the band found fascinating and appalling. Songwriter Evan Sult, “I think it’s a really true version of what it felt like to be alive, at least in Seattle [when] we actually wrote it. The ironic remove and the innate suspicion of both the mainstream culture and the alternative culture, and the yearning to be part of something, but not being able to get around the suspicion and the self-loathing. And then the ‘bah-bahs’ are just also the joy of being alive. It resonates with a frame of mind that turns out to be more universal than I would’ve thought. It’s both really upbeat and kind of savage and snarky at the same time.” It endures, as Graham Parker might say, because passion is no ordinary word.


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