In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.

The sensitive white guy with the acoustic guitar will never, ever die. Sensitive white guys have been picking up acoustic guitars for decades and decades. The archetype has been around, at the very least, since the ’50s folk revival, though god knows it might’ve already been a cliché by then. In the ’60s and ’70s, sensitive white guys with acoustic guitars became pop titans: Donovan, Paul Simon, James Taylor. (Bob Dylan was the prototype for all those guys, but Dylan was never especially sensitive.)

This century, sensitive white guys with acoustic guitars are no longer at the cultural vanguard. But something funny happened to that archetype in the ’00s. During the George W. Bush administration, a few sensitive white guys with acoustic guitars made chart-topping hits. But those sensitive white guys tended to be one-hit wonders, and their hits were goofy little cultural blips that could easily be dismissed as novelties. That’s what happened with James Blunt, with Daniel Powter, and with Plain White T’s.

Some caveats here: James Blunt wasn’t a one-hit wonder in his native UK, though he certainly was one here. Blunt served in the military, so he might not be that sensitive — though he did tell stories about playing his acoustic guitar while riding around on top of a tank, a truly insufferable image that might also represent a terrifying new mutation of the sensitive white guy with acoustic guitar type. Daniel Powter plays piano, not guitar, though he’s still a sensitive white guy with an acoustic guitar at heart. And Plain White T’s are a super-polished pop-punk band, not an acoustic-guitar situation. But “Hey There Delilah,” the band’s one hit, is a total sensitive acoustic-guitar white-guy song. It might be that decade’s purest example of the form.

Think of it. It’s all there — the basic fingerpicking with the soft string arrangement, the wounded cracking of the voice, the deeply goofy lovelorn lyrics that go for romanticism but come off a little deluded and jerky when you really think about them. “Hey There Delilah” was a random-ass stealth hit that took years to climb the Hot 100. Once upon a time, that was Paul Simon’s story. In a previous era, a song like that could’ve turned Plain White T’s leader Tom Higgenson into an actual star. But “Hey There Delilah” came out in 2005 and topped the Hot 100 in 2007, and it’s also not a very good song. Higgenson never stood a chance.

There really is a Delilah. Delilah DiCrescenzo is a professional distance runner who was never, ever romantically involved with Tom Higgenson or, for that matter, with any other Plain White T’s. Higgenson met DiCrescenzo at the Chicago House Of Blues in 2002. She was a student at Columbia in New York, and a mutual friend introduced her to Higgenson when she was back home on break. Higgenson was instantly smitten, and he told DiCrescenzo that he’d write her a song. She had a boyfriend, and she wasn’t interested. A while later, Higgenson dropped a CD off at DiCrescenzo’s house and told her to listen to it after he left. She did, and she heard “Hey There Delilah” for the first time. She was flattered, but she still wasn’t interested.

Tom Higgenson grew up in the Chicago suburb of Lombard, and he formed Plain White T’s with some high school friends in 1997. (Rod Stewart’s “Da Ya Think I’m Sexy?” was the #1 song in America when Higgenson was born.) I don’t know why Higgenson picked Plain White T’s as his band name, but that decision might’ve cost him a fortune in merch money. Why would anyone buy a T-shirt with “Plain White T’s” written on it when they could just buy an actual plain white tee?

This was back before Fall Out Boy was a thing, but late-’90s Chicago was already full of pop-punk bands who went for big, melodic emotion. If you listen to Plain White T’s’ self-released 2000 debut Come On Over, you can hear these kids shooting for a softer, more wistful version of the energetic tunefulness that scene elders like Alkaline Trio and the Lawrence Arms had already nailed.

Plain White T’s went through a bunch of lineup changes over the years, and they were mostly a local Chicago band until 2002. That’s when they signed with Fearless Records, a California indie that specialized in pop-punk and released early records from bands like At The Drive-In and Portugal. The Man. Fearless released Plain White T’s’ sophomore LP Stop. I don’t know when Tom Higgenson got the shaggy, floppy haircut that will always be associated with ’00s emo, but he definitely had it when Plain White T’s started making videos.

In 2005, Plain White T’s released All That We Needed, their second album on Fearless. Sean O’Keefe, one of the producers of that record, was a Chicago guy who’d become a big deal in the whole emo world. O’Keefe had already produced successful albums for Fall Out Boy, Motion City Soundtrack, and Hawthorne Heights. Those bands represented a whole new wave of wordy, pop-friendly guitar music that became a grassroots teenage phenomenon in the mid-’00s. Suddenly, a certain type of band was becoming hugely popular, seemingly overnight. The jeans were tight, the haircuts were feathery, the T-shirts were extra-medium, and the lyrics were usually about treacherous ex-girlfriends.

The whole MySpace emo wave was probably the last time that aggressive, guitar-driven rock-band music achieved any kind of centrality in youth culture. Emo acts like Jimmy Eat World and Dashboard Confessional had a lot of success in the early ’00s, but 2005 was the year that the wave really crested. That’s when Fall Out Boy, a Chicago band that later took Plain White T’s on tour, released their breakout album From Under The Cork Tree. That year, Fall Out Boy’s anthemic single “Sugar, We’re Goin Down” made it to #8. (It’s a 10.) Sean O’Keefe didn’t produce From Under The Cork Tree, but his involvement still put Plain White T’s in good company.

The other producer who worked on Plain White T’s’ All That We Needed was Ariel Rechtshaid, the former leader of a Los Angeles ska-punk band called the Hippos. By 2005, Rechtshaid was playing bass in the indie rock band Foreign Born. He was pretty new to production at the time, though he’d worked on New Jersey emo band Armor For Sleep’s 2003 debut. O’Keefe and Rechtshaid both knew what they were doing, and most of All That We Needed is a cleaner, more radio-friendly version of the pop-punk that Plain White T’s has already been making. The single “Take Me Away,” which sounds like junior-varsity Jimmy Eat World, is pretty typical of the whole record.

On its final track, though, All That We Needed takes a turn. That’s when we get “Hey There Delilah,” the only acoustic ballad on the LP. Tom Higgenson wrote that song about Delilah DiCrescenzo, but the song depicts a whole fictional and fantastical scenario where they’re actually together. On “Hey There Delilah,” Higgenson imagines himself in a long-distance relationship with Delilah. He’s in Chicago, and she’s in New York, but they’re still together in spirit: “Hey there Delilah, don’t you worry about the distance/ I’m right there if you get lonely, give this song another listen.”

Tom Higgenson promises that he’ll eventually “pay the bills with this guitar,” and he looks forward to the day when Delilah leaves New York for good: “Hey there Delilah, you be good, and don’t you miss me/ Two more years and you’ll be done with school/ And I’ll be making history like I do.” What the fuck is that line? He’ll be making history? Relax, buddy. Knowing what I know about the song’s genesis, I imagine “Hey There Delilah” as Higgenson’s last-ditch attempt to impress this girl and win her away from her boyfriend; the lyrics even have Higgenson describing the effect that he wants his music to have on her: “If every simple song I wrote to you would take your breath away, I’d write it all/ Even more in love with me, you’d fall.”

If Tom Higgenson’s goal was to woo Delilah DiCrescenzo, “Hey There Delilah” didn’t work. In a 2013 ESPN interview, Delilah talks about how she felt when she heard “Hey There Delilah”: “My first thought: ‘Oh no! Did I lead Tom on?’ I became anxious.” Delilah honestly worried that she’d given Tom Higgenson the wrong impression. If she’d been pissed off about his flights of lyrical fancy about her, she would’ve been justified. The chorus of “Hey There Delilah” is just Higgenson repeating the phrase “oh, it’s what you do to me” over and over. In that ESPN interview, Delilah says that her father heard the song and asked, “Delilah, exactly what did you do to this guy?”

I can kind of see why people would be drawn to “Hey There Delilah.” The song is plainspoken and specific — the uncommon first name and the New York references give the impression that Tom Higgenson is talking to a real person. One line gives him away, though: “Times Square can’t shine as bright as you.” Within their first month in town, New York college students learn to react with abject disgust whenever an out-of-towner so much as mentions Times Square. If “Hey There Delilah” came out today, maybe Higgenson would sub in “Dimes Square.”

“Hey There Delilah” has a simple, memorable melody, and it stands out — from the rest of the Plain White T’s album, from the rest of the 2005 emo class, and from the rest of the stuff that was on the radio at the time. But I think of the song as being profoundly wimpy, mostly for the way that Higgenson’s voice theatrically creaks throughout the song, as if he’s too emotionally overcome to sing properly. The song is fairly inoffensive. I never hated it, but I did find it boring and just slightly off-putting.

At first, “Hey There Delilah” was just an album closer. When Ariel Rechtshaid recorded the track, he didn’t think too much about it. Rechtshaid later told Sound On Sound, “I remember recording the vocals and the guitar separately, trying to make it sound like it was happening live — a very simple Beatles-y/Simon & Garfunkel kind of thing. I left it at that.” But “Hey There Delilah” picked up steam. It became a big singalong at Plain White T’s shows. In 2006, Fearless released Hey There Delilah EP with a few unreleased tracks and a live version of the song. On the live version, the crowd almost drowns Tom Higgenson out.

In 2006, Plain White T’s signed with the Disney-owned major label Hollywood Records, and they released their album Every Second Counts a year later. At that point, Plain White T’s were one of about a million emo bands who were surging in popularity. Every Second Counts mostly sounds even cleaner than All That We Needed, and Hollywood gave the band enough juice to cross over. Their lead single, the nasty post-breakup rage-out “Hate (I Really Don’t Like You)” became Plain White T’s’ first Hot 100 hit, peaking at #68.

But “Hey There Delilah” was the secret weapon. A couple of All That We Needed tracks reappear at the end of Every Second Counts, and one of them is “Hey There Delilah.” Plain White T’s made a “Hey There Delilah” video, with Tom Higgenson playing his acoustic guitar in an empty room and a model, playing Delilah, swanning around New York. The song started to catch on, and Ariel Rechtshaid remembers when it blew up: “All of a sudden, I started hearing it on the radio and thinking, ‘Is that even the same recording that I did?’ It was such a distant memory at that point. I kind of assumed that they’d re-recorded it. But it turned out that it was the same recording, and it came back to life and became a #1.”

Imagine how Delilah DiCrescenzo felt. At the time, she told USA Today, “When I’m at the gym, it’s playing. When I’m at the pool, it’s playing. Part of me wants to scream at the top of my lungs that it’s about me. Another part of me wants to cower and say it’s not.” For a while, she didn’t tell anyone that she was the Delilah of the song. Later, she told ESPN, “I was nervous that I’d let Tom’s fans down. They’d be disappointed to hear I have a boyfriend. Every girl would want a song written about her, and they’d think I was ungrateful and rude to deny Tom. I felt pressure to live up to those expectations.” Yikes.

Eventually, one of Delilah DiCrescenzo’s friends volunteered her for a radio interview. She didn’t want to admit that she was the Delilah, but she went along with it. Soon, Delilah was doing interviews all over the place; she later said that the whole process probably distracted her from her running. (Delilah made the 2008 Olympic trials, but she didn’t make the cut for the actual Olympic team.) Delilah wanted to bring publicity to her sport, and she also wanted to reassure her boyfriend that he didn’t need to feel jealous. Those interviews might’ve helped Delilah to get a Puma sponsorship, and they might’ve also helped push the song to #1.

Ultimately, “Hey There Delilah” was the only song from the whole mid-’00s emo wave that went all the way to #1. Other bands got bigger and scored more hits; a few of them — Fall Out Boy, My Chemical Romance, Paramore — can still fill arenas now. But “Hey There Delilah” had the advantage of not sounding like an emo song — of not having any audible punk influence at all. It sounded like Starbucks music, like Grey’s Anatomy music. The world accepted “Hey There Delilah” the same way that it had accepted James Blunt’s “You’re Beautiful” and Daniel Powter’s “Bad Day.”

Plain White T’s toured arenas in the fall of 2007, but they did it as one of Fall Out Boy’s opening acts. (I went to that tour when it came to Madison Square Garden, but I missed Plain White T’s, and I was OK with that.) Every Second Counts went gold, and the “Hey There Delilah” single eventually went quadruple platinum. The band’s follow-up single “Our Time Now” peaked at #90. Maybe that song title was a little premature.

“Hey There Delilah” got nominated for a couple of Grammys, including Song Of The Year, which it lost to Amy Winehouse’s “Rehab.” (“Rehab” peaked at #9. It’s a 9.) Delilah DiCrescenzo got her boyfriend’s blessing, and she went to the Grammys with Plain White T’s. Later, she told ESPN, “It was so much fun, despite being so out of my element. I swapped my sports bra and running shoes for a glamorous dress and expensive jewelry that, unfortunately, I had to return.”

Plain White T’s were never going to get anywhere near the level of “Hey There Delilah” again, but they kept making music, and they notched up a couple more minor hits. In 2008, they got to #34 with “1, 2, 3, 4,” the folksy single from their follow-up album Big Bad World. In 2010, “Rhythm Of Love,” another cutesy acoustic song, made it to #38. Both “1, 2, 3, 4” and “Rhythm Of Love” sounded like attempts to recapture what they’d already done with “Hey There Delilah.” Both of them failed, but both at least made the pop charts. Plain White T’s haven’t been back on the Hot 100 since.

After co-producing “Hey There Delilah,” Sean O’Keefe kept working, and he teamed back up with Fall Out Boy for their 2018 EP Lake Effect Kid. Ariel Rechtshaid went on to work with a bunch of exciting indie types: Cass McCombs, Glasser, Blood Orange. In 2012, Rechtshaid co-produced “Climax,” a masterpiece of a single from Usher, a guy who’s been in this column a bunch of times. (“Climax” peaked at #17.)

In 2013, Ariel Rechtshaid worked on a bunch of the year’s best albums: Sky Ferreira’s Night Time, My Time, Vampire Weekend’s Modern Vampires Of The City, Haim’s Days Are Gone, Solange’s True. At the end of that year, I interviewed Rechtshaid for Stereogum, and I thought he was cool as hell. Rechtshaid even humored me when I asked him if he was still spending that “Hey There Delilah” money. His answer: “No, that well has run dry. Maybe if I’d written it.” Rechtshaid has continued to do great work since then; just last month, he had a credit on the Caroline Polachek album.

I don’t know if Tom Higgenson is still spending that “Hey There Delilah” money. Plain White T’s are still going, though Higgenson is the only remaining original member. The band eventually parted ways with Hollywood Records, and they returned to their old label Fearless for their most recent LP, 2018’s Parallel Universe. In 2018, Higgenson was also talking about developing a “Hey There Delilah” TV show, adapting the song into a scripted romantic dramedy. I haven’t heard anything about the TV show since then; I wonder how Delilah DiCrescenzo will feel about the show if it ever comes out. Later this year, Plain White T’s will play the second edition of When We Were Young, the Las Vegas emo nostalgia-fest. That seems like the right place for them.

After “Hey There Delilah,” more sensitive white guys with acoustic guitars would come along, and some of them would even become major stars. This column will eventually have to deal with the whole Ed Sheeran situation.

GRADE: 4/10