Started from the Bottom: Week of 8/27/1988

Like most music enthusiasts, I love the Billboard charts - and like most music writers, I am constantly trying to think of different ways to look at and talk about pop music. In that spirit, I present a regular feature called Started from the Bottom, where I take a look at a random Hot 100 chart's lowest 10 entries. Are they classic hits on the way down? Future favorites just starting their run? Forgotten fun that never reached the highest heights? Come and take a look with me!

Hot 100 date: August 27, 1988

At the top: George Michael's "Monkey" - heavily remixed and improved by legendary production team Jimmy Jam & Terry Lewis - becomes the fourth and final No. 1 hit off his terrific 1987 solo debut Faith. Its predecessor, Steve Winwood's beer commercial soul "Roll with It," tumbles all the way to No. 7 after four weeks on top. The rest of the Top 10 is filled with surprisingly long lasting pop/rock acts (Elton John, Chicago), established '80s hitmakers (Huey Lewis & The News, Robert Palmer) and ascending stars (Whitney Houston, Tracy Chapman, Guns N' Roses - whose "Sweet Child O' Mine" will be the top song in America in two weeks' time).

100. Cyndi Lauper, "Hole in My Heart (All the Way to China)" (previously peaked at No. 54)

I'll never say a bad word about living legend Cyndi Lauper - She's So Unusual is one of the best pop debuts of the '80s, and True Colors has more bops than you may remember. (Justice for "Change of Heart"!) But audiences were tiring of what she was delivering by this part of the decade. "Hole in My Heart" is a great, fast-paced New Wave rocker saddled with a tough-to-digest lyric (the parenthetical almost dares the respondent synth line to get weirdly racist) and featured in the flop comedy Vibes, which starred Lauper and Jeff Goldblum as two psychics on a Romancing the Stone-esque adventure. The song is still weirdly hard to come by, not included on Lauper's next LP (1989's A Night to Remember) or any of her domestic hits albums. It was apparently a huge hit in Australia, however.

99. Poison, "Nothin' But a Good Time" (previously peaked at No. 6)

Arguably the critical and commercial apex of Poison's better-crafted-than-most hair-metal - and maybe, the whole so-dumb-it's-smart American wing of the subgenre itself - "Nothin' But a Good Time" is plain fun. You can almost hear these guys having a blast in the cracks of Tom Werman's production - little of the danger you'd hear in Guns N' Roses or Mötley Crüe.

98. Midnight Oil, "Beds Are Burning" (previously peaked at No. 17)

One of my favorite words to describe chart activity in the late '80s? Antipodean, which has nothing to do with single release planning and everything to do with how many acts were from Australia or New Zealand. INXS! Crowded House! Paul Kelly! And, of course, the signature hit from righteously-pissed group Midnight Oil, who got a tremendous land-back anthem into the American Top 20. Eat your heart out, Paul Hogan.

97. Al B. Sure!, "Nite and Day" (previously peaked at No. 7)

The rising New Jack sound wasn't limited to the Teddy Riley cinematic universe; in fact, the Guy mastermind only produced one track on the debut album from Al B. Sure!, a terrifically-stage-named soul striver from money-earnin' Mount Vernon who'd been discovered by Quincy Jones and cut his teeth as a backing vocalist for Heavy D. & The Boyz. (Sure's debut, In Effect Mode, was slated to be a rap record until he changed his mind and got really into crooning during production.) Sure, it's kind of all hook, but what a hook - and Al B.'s voice is smooth as they come. ("Nite and Day" is one of the few classic pop songs of its time that was also recorded in several languages!)

96. The Jets, "Make It Real" (previously peaked at No. 4)

The fifth and final Top 10 hit by the Minneapolis family band was, like the arguably better "You Got It All," a tuneful, shiny ballad that wouldn't be out of place at a chill high school dance or mall department store. Like most of their songs, it sneaks up on you, though, thanks mostly to Elizabeth Wolfgramm's vocal.

95. Natalie Cole, "When I Fall in Love" (chart debut)

Cole's rendition of this immortal pop standard, produced by Luther Vandross collaborator Marcus Miller (yes, that's Kenny G on the sax solo), sort of split the atom between her present and her future. "When I Fall in Love" was the second single from 1987's Everlasting, a commercial comeback after several years marred by drug addiction - but this was as high as it got on the charts, a bit of a disappointment after her previous single, a cover of Bruce Springsteen B-side "Pink Cadillac," hit the Top 5. But the placement didn't matter as much as the emotional resonance: "When I Fall in Love" was immortalized by Natalie's late father Nat "King" Cole, and in 1991 she would start a new chapter with her take on his "Unforgettable," a striking virtual duet with her father. (Five years later, she re-recorded this song in a more stately version, also with her dad's vocals in tow.)

94. Scritti Politti feat. Roger, "Boom! There She Was" (previously peaked at No. 53)

The music industry would be more interesting if maybe, at least, five acts a year could get the runway Scritti Politti did on their 1988 album Provision. Recorded over the better part of a year in 10 different studios across New York and London, the follow-up to the terrific Cupid & Psyche 85 (and its American hit "Perfect Way") found band members Green Gartside and David Gamson becoming fussy little studio tyros, putting their no-doubt generous production budget to the test with first-call studio ringers (guitarist Dann Huff, bassist Marcus Miller, percussionist Bashiri Johnson) and a few featured guests, including Miles Davis (who covered "Perfect Way") on "Oh Patti (Don't Feel Sorry for Loverboy)" and Zapp's Roger Troutman, whose distinctive talk box vocals are fleetingly heard on "Boom! There She Was." The result was what Gamson called "the most digital sounding analog record ever made" - pleasant enough, but I guess it's hard to improve on a single with the title "Perfect" in the title.

93. The Fabulous Thunderbirds, "Powerful Stuff" (chart debut)

I sincerely doubt that the late blues guitar legend Stevie Ray Vaughan got too bent out of shape about chart placement, but it might've tickled him a little that, three years after his acclaimed debut for Epic/CBS, The Fabulous Thunderbirds - a band featuring his older brother Jimmie on guitar - get signed to CBS Associated and take the blues-pop "Tuff Enuff" to the Top 20. (We know a certain young Connecticut guitarist blended SRV's style into 21st century pop at the beginning of his career, but by this chart logic, maybe Jimmie anticipated the rise of John Mayer.) That genre's success was never built to last long on the charts, as evidenced by the fairly standard "Powerful Stuff," a song no doubt eventually elevated to the mid-'60s on the Hot 100 thanks to its inclusion on the Cocktail soundtrack.

92. Rod Stewart, "Lost in You" (previously peaked at No. 12)

The opening track and lead single to Rod the Mod's splashy comeback Out of Order was eclipsed by its later singles "Forever Young" and "My Heart Can't Tell You No." But this is not to be missed! It lays down the intriguing thesis statement of "what if Rod Stewart had done a Power Station record?" (Three of that project's contributors - ex-Duran Duran guitarist/co-producer Andy Taylor and the CHIC rhythm section of producer/bassist Bernard Edwards and drummer Tony Thompson - are all over the record, with Taylor also co-writing this tune.) But it's also Rod playing the sentimental softie, too, abetted by an elegant string section in the refrain and the gentle mandolin of late session legend David Lindley. It's pretty dang good - that's a common-known, natural fact.

91. Robert Plant, "Ship of Fools" (chart debut)

As someone who was neither into Led Zeppelin as a teen or particularly keyed into singer Robert Plant's solo forays (at least, until his Grammy-winning collaborations with Alison Krauss in 2007 - which I quite like!), it's actually quite funny and intriguing to hear Plant go the closest to pop I can picture him doing. Now and Zen was indeed his bestselling solo album, bearing a patina of "he's back!" after ventures like The Honeydrippers and an ill-received semi-reunion of Zep at Live Aid. Part of that goodwill came from a reunion with guitarist Jimmy Page on the bigger hit "Tall Cool One," but I think the Tim Palmer-tastic rock-pop of "Ship" is where his heart really was at the time, and I prefer contemplative ballads like this to the posturing silliness of its predecessor.