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Welcome to the Chartcrush Top Ten Countdown Show, I’m your host, Christopher Verdesi. Each week on Chartcrush we dive deep into a different year in Pop music and pop culture history, and count down the top ten songs according to our recap of the weekly charts published in the music industry’s leading trade publication and chart authority, Billboard magazine.

This week we’re counting down 1988, Reagan’s last year, when Pop’s glossy ’80s makeover hit terminal velocity. Mall couture on full display—acid-wash denim, neon, spandex, shoulder pads. Big hair for women; Jheri-curls, high-top fades and mullets for men. Glam Metal Bands pounding arenas, veteran Boomers showing off their synth chops on million-selling albums.

MTV, still the oracle of cool, but just below the surface, the ground was shifting and whole new sensibilities were germinating as the generation that’d been driving and dominating pop culture since Ed Sullivan was aging out. No Baby Boomer in ’88 under 24, and Gen X, born ’65 to ’80—stirring, but still underground. What even was pop culture without Boomers?

Well the rough outlines were starting to resolve. In Rock, of course, the late ’80s were peak Glam Metal—Bon Jovi, Def Leppard, Poison. But left of the dial, college radio was seeding the future—Alternative Rock for the first-wave X-ers now in their late teens and early 20s. Once all the quirky Early ’80s New Wave Acts went mainstream—or tried to—college radio was where you had to go for stuff like The Replacements, Sonic Youth, Smiths and Pixies.

’87—the first year the entire 19-to-22 “college” demo was Gen X, and, no coincidence, ’87, also the year that U2 and R.E.M. became the first Alternative Acts to score top tens on the Hot100, so finally in September of ’88, Billboard launched its Modern Rock chart.

And in Hop-Hop: crossover top tens by Run DMC with Aerosmith and the Beastie Boys late ’86 and ’87, and eight other Rap songs charted on the Hot100 in ’87 with virtually no radio support beyond Rap stations in the biggest markets—KDAY in L.A., WBLS in New York. But once Hip-Hop did get a national showcase with Yo! MTV Raps in ’88, 15 Rap hits peaked on the Hot100—Fat Boys, LL Cool J, DJ Jazzy Jeff & The Fresh Prince, and Female newcomers Salt-n-Pepa and J.J. Fad.

At year’s end, Public Enemy’s It Takes a Nation of Millions to Hold Us Back won Album of the Year in the Village Voice‘s influential Pazz & Jop critics’ poll, and in ’89, Rap got its first weekly chart in Billboard.

Cassettes were how most Americans were buying their tunes in ’88—over half of music biz revenue from ’84 to ’89, and ’88 was the peak, with 450 million sold. And CDs outsold vinyl for the first time in ’88. But no one was sitting out music’s portability revolution—Walkman on your hip; cassette deck in the car, boombox if you wanted everyone to hear! 400 million blank Maxell, TDK and Memorex C-60 or C-90 cassettes sold as home taping culture thrived, foreshadowing the filesharing debacle that gutted the music biz in the ’00.

So ’88—both the zenith of ’80s flash and spectacle and the rumblings of Gen-X battering the ramparts, even as the year’s biggest hits were still within the Boomer-dominated mainstream.

#10 George Harrison – Got My Mind Set on You

Like our #10 song as we kick off the countdown. What could possibly be more within that Boomer comfort zone than a former Beatle? But like an exclamation point on our generational change theme, it was the last #1 by a Beatle. At #10, one of the most surprising comebacks in Pop history, it’s George Harrison’s “Got My Mind Set on You.”

George Harrison’s “Got My Mind Set on You,” #1 for one week in January and #10 on our Chartcrush countdown of 1988’s biggest hits—the last Beatles solo record to get to—not just #1, but the top 20! In the ’90s it took all three to score a hit—Paul, George and Ringo reuniting in the studio in ’95 with John Lennon’s cassette demos recorded in the ’70s and with Jeff Lynne’s help, forging new Beatles singles “Free as a Bird” and “Real Love.”

“Got My Mind Set on You” was a cover of an obscure R&B record George had bought while visiting his sister in America in 1963 just months before the Fab Four arrived in New York and Beatlemania erupted—the lead single off his first album in five years, Cloud Nine. After his ’82 album Gone Troppo bricked, he’d shifted to car racing and producing movies, but in ’87 he caught the music bug again and teamed up with Beatles superfan Jeff Lynne—whose distinctive ELO sheen is all over Cloud Nine, not to mention those aforementioned ’90s Beatles reunion hits.

And they weren’t done. While Cloud Nine was still on the charts, Harrison and Lynne were back in the studio, this time with Bob Dylan, Roy Orbison and Tom Petty as The Traveling Wilburys whose album dropped in the Fall, and went triple-platinum.

#9 Guns ‘n Roses – Sweet Child o’ Mine

So Glam Metal or “Hair Metal,” again, at full roar after Bon Jovi’s Slippery When Wet logged 38 weeks in the album chart’s top five, followed by five more Metal acts. Bon Jovi’s “Livin’ on a Prayer” and Whitesnake’s “Here I Go Again” both hit #1 in ’87, and two of the seven hits off Def Leppard’s Hysteria actually charted higher on the Hot100 than on Billboard‘s Rock chart.

But by ’88 Rock fans were craving something grittier—more street than salon. Enter our #9 Act, whose debut Appetite for Destruction spawned three top tens, the first topping the Hot100 for two weeks in September. Billboard‘s #1 New Artist of 1988, it’s Guns n’ Roses, “Sweet Child o’ Mine.”

Guns n’ Roses, “Sweet Child o’ Mine” from their 1987 album Appetite for Destruction—the bestselling debut album ever: 30 million sold, 18 million in the U.S. Raw Punk edge colliding with Hollywood sleaze and igniting Rock’s zeitgeist like a cigarette butt flicked into hairspray factory.

“Sweet Child o’ Mine,” an outlier—Axl Rose’s tender ode to girlfriend Erin Everly, daughter of Don Everly of the Everly Brothers. Two more top tens followed—”Welcome to the Jungle” and “Paradise City“—and suddenly Bon Jovi sounded too slick and Def Leppard, too Pop. Glam had peaked. Metal’s next big wave? Thrash, already pushing at the ramparts in ’88, but still underground ’til Metallica’s Black Album in ’91, the same year Nirvana crashed in with Grunge.

#8 Tiffany – Could’ve Been

But before Metal’s next chapter could roar in, America’s malls had other plans, and at #8 on our 1988 edition of the Chartcrush Top Ten Countdown Show, the second #1 in just three months by a brand-new Teen Idol, just 15 when she cut her first album. And when the label started having second thoughts about releasing it, her Producer-Manager sent her out on a nationwide tour of, yes, shopping malls. And it worked—spectacularly. At #8 it’s Tiffany with “Could’ve Been.”

Tiffany, “Could’ve Been,” a #1 on both Pop and Adult Contemporary in ’88. Not bad for a Singer who’d just broken through covering ’60s Bubblegum hits in food courts. But the song was written by a Boomer, Singer-Songwriter Lois Blaisch, and Tiffany’s version we just heard at #8 has the same backing track as Blaisch’s 1983 demo.

Could she have prolonged her hot streak leaning in to AC perhaps? Doubtful. Her next Ballad single “All This Time” barely grazed the AC top ten, and with Mariah Carey and Celine Dion right around the corner, things were about to get very crowded in that lane. But ditto Teen Pop: rival Debbie Gibson not just Singing but writing her own hits, and Paula Abdul, Martika, Kylie Minogue and Tiff’s own opening act, New Kids on the Block queued up for ’89.

Add in a messy emancipation battle with her parents, and Tiffany’s run was over by mid-’89, though she never stopped recording and resurfacing on nostalgia tours, reality shows, B-movies—even an “all grown up” Playboy spread in 2002.

#7 Rick Astley – Never Gonna Give You Up

Which raised a lot of eyebrows for sure, but nothing compared to how our song and Singer at #7 resurfaced later in the ’00s as the internet hit warp speed—and he didn’t even have to lift a finger! Details on that straight ahead, but first the song: a British Singer-Songwriter whose deep, soulful voice was something fresh in late ’80s Dance Pop and Adult Contemporary. Four top tens from ’87 to ’89 and the biggest was the first: #1 for two weeks in March. At #7 as we count down the top ten hits of 1988 here on this week’s Chartcrush, it’s Rick Astley’s “Never Gonna Give You Up.”

Rick Astley’s “Never Gonna Give You Up” at #7, Billboard‘s top-selling 12-inch single of ’88, and Astley named the #1 Dance Club Play Artist of the Year—but so frozen in its 1988 moment that beyond class reunions, retro nights and “worst of” lists—like VH1’s “Most Awesomely Bad” in 2004 and then a gag in an episode of It’s Always Sunny in Philadelphia—there wasn’t much reason to revisit it.

Until Rickrolling. Click a link in a webpage or email, hit “next slide” in a PowerPoint—boom! Instead of what you expected, it’s Rick Astley in a trench coat in the “Never Gonna Give You Up” video. Gotcha! You’ve been Rickrolled. Church of Scientology links, a favorite target—Astley loved that.

And the capper? November ’08 when online pranksters stuffed MTV Europe’s “Best Act Ever” ballot box with millions of votes for Astley—and he won, but he skipped the ceremony, leaving Katy Perry and Perez Hilton to present the award without him!

#6 Bobby Brown – My Prerogative

Well we’re counting down the top ten hits of 1988 here on this week’s edition of the Chartcrush Top Ten Countdown Show, and up next at #6 we have the first of three songs in our countdown that Billboard had in their 1989 year-end Hot100, not ’88.

Their rule in the late ’80s—and bear with me here: if a song is still climbing at the end of their chart year—usually around Thanksgiving—its full chart run counted in the following year’s tally. But if it had peaked and was heading down, its run so far counted in the current year, plus Billboard‘s estimate of its remaining chart life. The goal: to keep year-end charts from short-changing big hits whose runs straddled two calendar years.

Now here at Chartcrush with the luxury of hindsight and not having to make a press deadline, we get to factor every song’s actual full chart run, and go by calendar years, not arbitrary date-shifted “chart years,” and songs gets ranked in whichever calendar year they racked up the most points. So this next one at #6—it hadn’t cracked the top ten by the end of Billboard‘s 1988 chart year, December 3, but it did the very next week, and by a slim margin, it earned more points in calendar ’88 than ’89, so that’s where we’ve got it—at #6 for 1988. Again, the first of three like that in our ’88 top ten.

It’s from the “bad boy” of ’80s R&B Boy Band New Edition, breaking out solo with a defiant statement of independence that helped launch Producer Teddy Riley’s hot new R&B/Hip-Hop hybrid New Jack Swing. Billboard‘s #2 song of 1989, our #6 for ’88, it’s Bobby Brown’s “My Prerogative.”

Bobby Brown, “My Prerogative,” #6 as we count down the top ten hits of 1988 on this week’s Chartcrush Top Ten Countdown Show. Brown’s old Group New Edition had written the Boy Band playbook in the ’80s, but with his album Don’t Be Cruel, at 18, Bobby was the first New Edition alum to make the leap from Teen Idol to adult Pop Star—as it turned out, the first of many.

Of the album’s five top tens, “My Prerogative” was his manifesto—a swaggering kiss-off to anyone questioning his choices. And those choices kept him in the headlines for years—stormy marriage to Whitney Houston in ’92, drug arrests, rehab stints, and finally in 2005, Being Bobby Brown, the Bravo! reality show that turned their chaos into must-see TV.

#5 George Michael – One More Try

And speaking of Artists breaking out of their Teen Idol image, next up, the Singer from the mid-’80s British Pop Duo Wham! who scored our #1 song of 1987 with the title track off his debut solo album, Faith. “Father Figure” was the second #1 off that album in March of ’88, and then this Soulful Ballad at #5 in our countdown—the third: #1 for three weeks, May into June.

And the week it dropped out of the top spot on the Hot100, it topped the R&B chart, which was a huge deal for a British Singer-Songwriter obsessed with American Soul. Not only did he write all the songs on Faith; he also produced and played all the instruments! At #5 it’s George Michael’s biggest hit of ’88, “One More Try.”

Nearly six minutes, George Michael’s “One More Try” at #5 in our Chartcrush Top Ten Countdown for 1988. He refused to do a single edit, but radio still played it.

Now looking back it seems obvious that George Michael’s songs were about relationships with other men, even though he didn’t actually come out as Gay until his arrest in ’98 for “lewd acts” in a public bathroom in L.A. But in the era of “don’t ask, don’t tell,” even flamboyant Acts like The Village People, Boy George or Frankie Goes to Hollywood—not to mention David Bowie and Elton John—were mostly read as parody, fashion gimmicks, tongue-in-cheek fun, not identity. And George Michael used that wide berth as a lyrical canvas, writing love songs that spoke his truth long before he could say it out loud.

#4 INXS – Need You Tonight

Now as I mentioned at the top of the show, by ’88, that New Wave spark of MTV’s early days—those quirky, Punk-adjacent sounds from ’81 to ’84: all but gone. Some Acts fizzled; others chased glossy Pop and lost their edge. But a handful kept their cool and transitioned to Alt Rock and Billboard‘s Modern Rock chart launched in ’88. Among them these guys—eight top tens on that new chart between ’88 and ’93.

This one was a hit early in ’88 before the chart existed, but it kicked off a run of six consecutive top tens on the Hot100 through ’91. U2 may’ve been the biggest New Wave survivors in the late ’80s, but right behind them, Billboard’s #1 Pop Singles Artist of 1988. At #4 it’s Australia’s INXS with “Need You Tonight.”

“Need You Tonight,” the lead single off INXS’s quadruple-platinum album Kick, #1 for a week at the end of January. Then came the top tens “Devil Inside,” “New Sensation” and “Never Tear Us Apart,” and suddenly they were everywhere. In the Fall they owned the MTV Video Music awards—Rolling Stone calling their performance “the sexiest five minutes on MTV,” while Critics compared Frontman Michael Hutchence to Mick Jagger and Jim Morrison, and music mags put him—solo—on their covers.

That momentum carried deep into the ’90s until Hutchence’s suicide in ’97 stopped them cold. Seven years later, they tried to reboot on the CBS reality show Rock Star: INXS, even scored a modest hit with “Pretty Vegas” with the winner J.D. Fortune singing, but by then, the Pop landscape they’d ruled in ’88 had vanished—and along with it (at least on the charts), the stylish, reckless, swaggering type of Rock star that Hutchence embodied.

#3 Chicago – Look Away

Okay, down to the top three, and back-to-back at numbers 3 and 2, the other two songs in our Chartcrush Top Ten for 1988 in that dense cluster of big hits at the end of the year, that when Billboard unveiled its 1989 year-end Hot100, everyone went “wait, weren’t those on the radio last year!” “My Prerogative” we heard back at #6 was Billboard‘s #2 song of 1989—but this next one was #1. And its two weeks at #1? December of ’88!

Cue collective head shaking and facepalms, and after the uproar, Billboard scrapped its “count the full chart run” method it’d used since ’86 and went back to splitting points between chart years for year-straddling hits for its year-end charts.

So what’s the song that caused all the fuss? Well, here it is, #3 on our 1988 ranking: a Chicago Power Ballad sung not by Peter Cetera, who’d gone on to solo glory, but by Bill Champlin. It’s Diane Warren’s second #1 as a Songwriter after Starship’s “Nothing’s Gonna Stop Us Now” in ’87, “Look Away.”

“My Prerogative” and New Jack Swing—still fresh at the end of ’89 even though the song was an ’88 holdover. But after a year of Paula Abdul and Milli Vanilli in ’89, a Chicago Power Ballad at #1 for the year wasn’t on anyone’s bingo card, so fans and critics alike bristled.

Still, an impressive feat to jettison Peter Cetera and score a #1 hit, and that’s what Chicago did in ’88 with “Look Away.” Cetera scored hits too, of course: “Glory of Love” from Karate Kid Part 2, #1 in 1986, and his duet with Amy Grant, “The Next Time I Fall,” also topped the chart.

#2 Poison – Every Rose Has Its Thorn

Up next at #2, the second in our twofer of late-in-the-year smashes that Billboard ranked in its 1989 year-end Hot100 but by our math here on the Chartcrush Top Ten Countdown Show, scored more points in calendar 1988. It didn’t sound as dated as “Look Away” when it turned up on that ’89 year-end list because, like “My Prerogative,” it was something new: a makeup-caked Hair Metal Band known for punky bangers like their 1987 debut “Talk Dirty to Me,” suddenly out with a stripped down acoustic Message Song. Their first and only #1, three weeks spanning December into January ’89, Poison’s “Every Rose Has Its Thorn.”

“Every Rose Has Its Thorn,” Poison. #2 on our countdown of the top ten hits of 1988 here on The Chartcrush Top Ten Countdown Show. The Acoustic Power Ballad wasn’t new, of course. KISS, Night Ranger, Warrant, White Lion, they’d all gone there, but Poison’s pivot landed like a midlife reckoning: Glam Metal after a decade of wild debauchery, hairspray and pyrotechnics. Within a year MTV launched Unplugged, and even KISS was baring its soul on a stool.

Poison tried it again on their next album in 1990 and got to #4 with “Something to Believe In,” and Extreme stripped things down even further on their #1 in ’91, “More Than Words,” but then the ground shifted with Grunge and Thrash and that was pretty much it for Glam Metal in the top ten.

#1 Steve Winwood – Roll with It

Up next, our #1 song of ’88, and its June to October chart run also landed it in Billboard‘s year-end top ten for ’88—but at #10. Why #10? Well we can’t say for sure since Billboard was factoring unpublished data in its algorithm behind the scenes in the last few years before ditching their 40-year-old survey system and going to actual sales and airplay tallies from Soundscan and Broadcast Data Systems for the 1992 chart year. That underlying data—not public either.

But at Chartcrush we stick to a consistent formula for ranking all years that’s based solely on Billboard‘s published weekly charts—and surprise! Their #10 comes out #1! It’s close—only a few points separated our top three—but four weeks at #1, the most of any ’88 hit, puts it over the top, just barely.

It’s a veteran English Rocker since the ’60s—Spencer Davis Group, Blind Faith, Traffic—now Nashville-based with his American second wife—and the late ’80s were his chart zenith. At #1, it’s Steve Winwood’s second career chart topper after “Higher Love” in ’86, “Roll with It.”

Steve Winwood’s “Roll with It”—our #1 song of 1988—was also the final #1 of Casey Kasem’s original run hosting American Top 40, his syndicated radio countdown since 1970. That’s a tidy punctuation on our generational change theme here on our 1988 edition of Chartcrush. It also topped the Adult Contemporary and Mainstream Rock charts, and was Winwood’s first R&B chart entry since The Spencer Davis Group’s “I’m a Man” in 1967. Oh, and it won him the Grammy for Best Male Pop Vocal Performance.

His Michelob Beer Commercial song “Don’t You Know What the Night Can Do?” also cracked the top ten later in ’88, but from there the hits tapered off, although his 2008 album Nine Lives featuring an Eric Clapton collab debuted at #12—the highest of his career.

Bonus

So that’s our Chartcrush Top Ten, but with all this calendar-year shuffling I’ve been calling out, no surprise that Billboard‘s year-end list doesn’t line up exactly. First, the big one I haven’t mentioned yet: Billboard‘s #1 song of ’88, George Michael’s “Faith.” That, plus their #6 and #7—Whitney Houston’s “So Emotional” and Belinda Carlisle’s “Heaven Is a Place on Earth“—were all late ’87 hits that shift into our ’87 ranking when you go strictly by calendar years.

Then, coming in from Billboard‘s 1989 year-end top ten: Chicago’s “Look Away,” Bobby Brown’s “My Prerogative,” and Poison’s “Every Rose Has Its Thorn.” Those were Billboard‘s top three songs of 1989—but really, they’re ’88 hits.

So, three shuffling out to ’87, three coming in from ’89—well you’d think that evens things out, right? Not quite. There’s still one song from Billboard‘s 1988 year-end top ten that got nudged out of ours just from the way we crunch the numbers.

#21 Breathe – Hands to Heaven

It was their #9 song that racked up 29 weeks on the chart—just one shy of Taylor Dayne’s 30 with “I’ll Always Love You:” the British Sophisti-Pop Group Breathe with “Hands to Heaven.”

Breathe’s “Hands to Heaven” never hit #1 and only had six weeks in the top ten—most of our 1988 Chartcrush hits had seven or eight—yet Billboard ranked it #9 on the year. We’ve got it at #21. Again, Billboard‘s ’88 rankings factored undisclosed data; ours are based purely on weekly chart action.

The one song we heard in our countdown that wasn’t in any Billboard year-end top ten: George Michael’s “One More Try.” They had that one at #11 for ’88.

#22 Anita Baker – Giving You the Best That I Got

And finally in our ’88 edition of Chartcrush, two more songs from Billboard‘s 1989 year-end top ten that were really 1988 hits—five in all, if you’re keeping count. No wonder Billboard went back to splitting chart runs!

At #10 for ’89, the track Chicago Bulls legend Michael Jordan blasted in the locker room before games. Not exactly “Eye of the Tiger“—more smooth, romantic, Jazzy. The sound of late-’80s Adult Contemporary: Quiet Storm. Anita Baker, “Giving You the Best That I Got.”

Anita Baker’s “Giving You the Best That I Got”—peaked at #3 in that jam-packed hit cluster in late ’88. Billboard‘s #10 hit of 1989; on our Chartcrush ’88 ranking, it’s #22.

#15 Will to Power – Baby, I Love Your Way/Freebird Medley

And Billboard‘s #9 song of ’89—also an ’88 hit, but not big enough to crack our Chartcrush Top Ten. On our ’88 ranking it notches in at #15. It’s a medley of two songs that are unrelated except that they’re both Rock cuts from the ’70. Miami DJ-Producer Bob Rosenberg heard one on the radio and it made him think of the other. And under label pressure to make an album, the “Baby I Love Your Way/Freebird Medley” was born. It’s Will to Power.

Will to Power’s “Free Baby Medley,” fusing parts of two mid-’70s Rock classics into a conversation between Lovers—Singer Suzi Carr singing Peter Frampton’s “Baby, I Love Your Way” about missing your partner, and Producer/Mastermind Bob Rosenberg singing Lynyrd Skynyrd’s “Free Bird” about not wanting to be tied down—and it somehow connected and was Billboard‘s #9 hit of 1989; #15 on our Chartcrush ranking for 1988, the calendar year it saw most of its chart action.

And with that, we’re gonna have to wrap up our action-packed 1988 edition of the Chartcrush Top Ten Countdown Show, but hey, if you like what you heard and want more, head on over to our website, chartcrush.com for a written transcript of the show and a link to stream the expanded podcast edition, plus dope extras like our full top 100 chart and interactive line graph of the actual chart runs of the top ten songs. We do all that for every year we count down, from the 1940s to now, and it’s all on that website, again, chartcrush.com.

I’ve been your host, Christopher Verdesi. Thanks for listening, and tune in again next week for another year, and another edition of Chartcrush.

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