Adam Schlesinger's 15 Greatest Songs: Fountains of Wayne, 'That Thing You Do!,' 'Crazy Ex Girlfriend' & More (Staff Picks)

Adam Schlesinger
Ebet Roberts/Redferns

Adam Schlesinger of Fountains Of Wayne at his home studio in New York City on April 11, 1999.

Adam Schlesinger didn’t just understand what made a perfect pop song tick; he could map its genome and replicate it like a mad scientist. From his early hits with Fountains of Wayne to his work in TV and film and for outside artists, he had a chameleon-like ability to apply his musical understanding to any context.

“On an artistic level, the only people that you really have to fight with are the people in your own band,” Schlesinger, who died at 52 Wednesday morning (April 1) of coronavirus complications, told Pop Matters in 2010. “If you're working on a movie or a TV show or something, you're really just trying to deliver what somebody else wants and read their minds.”

That musical telepathy not only led to Fountains of Wayne’s No. 21 hit “Stacy’s Mom” and fan favorites like “Hackensack,” but enduring outside assignments for VHS-era hits like 1996’s That Thing You Do! and 2000's Josie and the Pussycats, as well as songs recorded by the Monkees, the Click Five, and the Jonas Brothers.

To mark a musical genius’s tragic passing, Billboard is looking back at his 15 most essential songs.

Fountains of Wayne, "Radiation Vibe" (Fountains of Wayne, 1996)

The first song on Fountains of Wayne’s self-titled debut is a slacker-y delight with zonked nonsense verse typical of the era: “Are you alone now/ Did you lose the monkey/ He gave you backaches/ And now you slouch.” “It’s got some kind of magic, fun quality to it that we never really had in anything before,” Schlesinger told The A.V. Club in 2011. “I got very jealous of that song.” While “Radiation Vibe” was actually written by co-leader Chris Collingwood rather than Schlesinger, it showed that Fountains of Wayne nailed its effervescent sound from the jump. -- MORGAN ENOS

Fountains of Wayne, "Sink to the Bottom" (Fountains of Wayne, 1996)

“Sink to the Bottom” failed to chart stateside, but did respectably in the U.K., peaking at No. 42 and (oddly enough) hitting the top 10 in Finland. "Apparently, it was in some Finnish beer commercial,” Schlesinger was quick to add to the A.V. Club. “I think No. 7 in Finland is literally about 1,000 records, so we've been living off that for a while.” His self-deprecation aside, it’s hard to think of a more prototypically 1996 radio-rock song than “Sink to the Bottom” -- despondent yet triumphant with a melodic fuzzbomb of a chorus. -- M.E.

The Wonders, "That Thing You Do!" (That Thing You Do!, 1996)

The musical centerpiece from the Tom Hanks-directed '60s-set comedy of the same name is more than just a theme song: It's a central character, an action sequence, a love story, a rise and a fall in 166 glorious seconds. No soundtrack song has ever turned its parent movie from an above-average rom-com into a must-watch cable classic with greater velocity; it not only pays worthy tribute to the British Invasion-era one-offs it's patterned after, it roundly out-fabs nearly all of 'em. Just one of a hundred perfect moments: When the end of the opening couplet -- "You, doing that thing you do/ Breakin' my heart in two" -- is actually revealed not to be "in two" but "into," as in "into a million pieces, like you always do," complete with stunning melodic and shift and gorgeously supportive harmonies. -- ANDREW UNTERBERGER

Fountains of Wayne, "Denise" (Utopia Parkway, 1999)

This carbonated 4/4 jam with wheedly synths has a sneaky way with detail about its titular love interest (“She drives a Lavender Lexus/ She lives in Queens/ But her dad lives in Texas”) and her day job (“She works at Liberty Travel/ I hear her heart’s made of gravel”). As a character study, “Denise” is more silly and whimsical than substantial, but it’s a great example of how Schlesinger, with seeming effortlessness, could write a power-pop melody that made you weak in the knees. -- M.E.

Josie and the Pussycats, "Pretend to Be Nice" (Josie and the Pussycats, 2000)

Schlesinger often used the movies he wrote for as a chance to write the fake arena-conquering pop-rock anthems that might not have made so much sense for his own real-life band. "Pretend to Be Nice," for the faux-phenoms of the cult classic film adaptation of Josie and the Pussycats, feels so antsy for such six-string glory that it doesn't even waste a second before launching in into the glam-pop crunch of its first verse, not relenting until the unexpected pull-back of the lovelorn chorus: "Can't you just pretend to be nice?" By then, the song (and the Pussycats) are already in the stratosphere. -- A.U.

Fountains of Wayne, "Stacy's Mom" (Welcome Interstate Managers, 2003)

"One of my best friends, when we were maybe 11 or 12, came to me and announced that he thought my grandmother was hot,” Schlesinger informed MTV News in 2003 about the origins of “Stacy’s Mom.” “I said, 'Hey, you're stepping over the line,' but at that point in life, I wouldn't put it past anyone." Featuring an intro that tips its hat to The Cars’ “Just What I Needed,” the quirky, slick, and ultimately ubiquitous hit shot to No. 21 on the Hot 100 and remains Fountains of Wayne’s best-recognized song. At its essence, it’s “about that period when you're first hitting puberty and suddenly everybody of the opposite sex is strangely attractive," Schlesinger explained, and while “Stacy’s Mom” comes off as rather brazen in 2020, you can’t say Schlesinger didn’t tap into a universal human experience -- over Ocasek-worthy guitars and synths, no less. -- M.E.

Fountains of Wayne, "Hackensack" (Welcome Interstate Managers, 2003)

Like fellow one-hit wonders Harvey Danger with “Flagpole Sitta,” the Fountains of Wayne conversation is so dominated by “Stacy’s Mom” that their mellower, deeper material doesn’t get much ink. Today, “Hackensack,” written from the perspective of a Bergen County townie who pines over an actress he grew up with who moved to L.A., comes across less like the work of a wacky power pop band than a deep cut by Yo La Tengo. For anyone who thinks Wayne was a one-trick pony, “Hackensack” is the antidote, and no less a top 40 authority than Katy Perry has confirmed as much. -- M.E.

Ivy, "Thinking About You" (In the Clear, 2005)

No song titled "Thinking About You" has ever been bad, and better believe Adam Schlesinger's group wasn't about to break that streak. A lush synth-rock concoction of such heart-rending upbeat melancholy that you can't help searching for Robert Smith's name in the credits, the Dominique Durant-sung ode to a lost love is so wistful and smiling-through-its-tears that it almost has to be about something way more final than a breakup. The emotionally muted, almost shrinking vocal packs an impossibly mighty wallop as it reaches the final conclusion of the chorus: "And you're fading to black/ Like it's nothing at all." -- A.U.

The Click Five, "Just the Girl" (Greetings From Imrie House, 2005)

The trick answer to the trivia question "What was Adam Schlesinger's biggest Billboard hit?" The Click Five were a young Boston pop-rock fivepiece designed to generate Beatlemania-type hysteria, sort of inventing themselves as the real-life 21st century version of The Wonders from That Thing You Do! Luckily, they also had the Adam Schlesinger song to do it with: "Just the Girl," an instantly winning pop-not-quite-punk lift-off with inspired lyrical turns like "She laughs at my dreams/ But I dream of her laughter." Unfortunately for The Click Five, the Wonders parallels were a little too real: After "Just the Girl" peaked at No. 11 on the Hot 100, they never hit the chart again. -- A.U.

Fountains of Wayne, “Traffic and Weather” (Traffic and Weather, 2007)

While most of Fountains of Wayne’s well-known songs are front-loaded in their first three albums, the remaining two, Traffic and Weather and Sky Full of Holes, are remarkably strong. Schlesinger had a Stephin Merritt-like ability to mine bottom-of-the-barrel metaphors for comedic-heartfelt effect, and Traffic and Weather’s title track -- written about two newscasters in love who belong together like, well, you know -- is a prime example. -- M.E.

America, "Work to Do" (Music & Lyrics, 2007)

"PoP! Goes My Heart" gets the most attention (deservedly), and "Way Back Into Love" gets the most screentime, but the secret musical highlight of Hugh Grant/Drew Barrymore romantic comedy Music and Lyrics is this ending-credits gem. A sighing jangle-pop beaut of immaculate structure and production (and a addictive little wheeze-synth hook), Schlesinger generously gifted "Work to Do" to '70s soft-rockers America, who'd delivered their own share of gentle pop-rock KOs in their day. Inexplicably, "Work" was left off the movie's official soundtrack. -- A.U.

Tinted Windows, "Kind of a Girl" (Tinted Windows, 2009)

Combine members of Cheap Trick, Smashing Pumpkins, Hanson and Fountains of Wayne -- with their decades' worth of undeniable crossover hits between them -- and you knew they were gonna produce at least one stone classic between 'em. Tinted Windows got theirs with the electrifying, whoa-whoa-tastic "Kind of a Girl," an infatuation anthem buzzing with the kind of energy and craft that can only be produced by a quartet of pop-rock lifers getting to do exactly what they always wanted to do with a supporting cast of kindred spirits. Released in 2009, at the height of Kings of Leon and the Black Eyed Peas, the mainstream rock and pop worlds both politely passed -- unsurprising, but still a shame. -- A.U.

Fountains of Wayne, "Someone's Gonna Break Your Heart" (Sky Full of Holes, 2011)

Fountains of Wayne’s final album, Sky Full of Holes, more closely resembles Schlesinger’s second act as a master craftsman than a wacky novelty songwriter. While “Someone’s Gonna Break Your Heart” starts with a silly image he couldn’t resist (“Staring at the sun with no pants on”), it flips into poignancy quickly, with one of the band’s most all-the-way-there melodies in the chorus and a series of fleeting images: The imaginary airport breeze/ It flickers and flows/ Fans fires in the road/ All we want to do is go home.” -- M.E.

Rachel Bloom, "You Stupid B--ch" (Crazy Ex-Girlfriend, 2016)

"You ruined everything you stupid, stupid b--ch–/ You're just a lying little b--ch who ruins things and wants the world to burn." Words you might hear in any number of songs, but in a heartfelt piano ballad that sounds like it's coming from a powerhouse diva projecting her voice to an adoring arena? And wait, it's not sung to an ex-lover, but to herself? This is Exhibit A of Crazy Ex-Girlfriend's ability to plumb the uncomfortable depths of obsessive self-loathing while still making you belly laugh. And Schlesinger's production work -- complete with a rush of canned applause at the start, as if the "live" audience knows this smash hit and has been waiting for it -- demonstrates his attention to the minute details of recorded music history. -- JOE LYNCH

Rachel Bloom, "The Math of Love Triangles" (Crazy Ex-Girlfriend, 2016)

An almost too-perfect send-up of the ditzy vocal jazz chanteuse archetype, "The Math of Love Triangles" finds Crazy Ex-Girlfriend star Rachel Bloom taking a cue from Marilyn Monroe a la "Diamonds Are a Girls Best Friend" while trading math puns with a chorus of dapper gay men: "I'll be swinging from a hypote-noose," "We're tired of all your tangents" and "Ooh, are you erect?" "No, 90 degrees" all add up to a song that is equal to or greater than the vast majority of parody material. -- J.L.