Welcome to 1999 Music Week, a celebration of one of the most interesting, vivid, varied music years ever. Join us as we count down the best singles and albums of the year, remember the days of scrubs and the girls who wear Abercrombie & Fitch, and argue about which albums stood above the rest.

When Marcos Siega was hired to direct the video for the first single off of Blink-182’s third studio album, the filmmaker struggled to think of a clever idea. “I didn’t know them personally,” he said. “But I had listened to them. I knew who they were. I kind of got their sensibilities.” Eventually, his mind went to a late-night television clip of a streaker. That led to him picturing the band in their birthday suits.

Welcome to 1999 Music Week Join us as we travel back 20 years to explore a fascinating time in pop music

“I’m like, ‘Oh, that’s funny,’” Siega said. “‘They just run around naked.’” The concept was easy to sell to the suburban San Diego trio’s exhibitionist co-frontmen Tom DeLonge and Mark Hoppus. (Shy drummer Travis Barker needed convincing.) Wary of indecent exposure laws, the group spent some of the shoot sprinting through Los Angeles in skin-colored Speedos. But in between joining a pickup basketball game, bumping into adult actress Janine Lindemulder (more on her later), and interrupting a taping of Talk Soup, they performed on a stark-white stage—covered up only by their instruments.

“My brain kept going to the sort of anti-establishment punk rock ethic that I associated them with,” said Siega, who hoped that Blink would gain exposure by exposing themselves. “But not in an aggro way. They always came across to me as doing it with a wink. They were fun.”

The clip, made to promote the ode to arrested development “What’s My Age Again?,” captures Blink-182’s gleefully juvenile shtick. “If you gave a 14-year-old kid a microphone and a bunch of people to say something in front of, what would he say?” Hoppus told Entertainment Weekly in 2000. “That’s us. Although I’m 27.” The quip actually undersells the band’s powers. At their peak, Blink-182 put out music that sounded like it was conceived by teenagers who’d been mainlining a mixture of Mountain Dew concentrate and Super Songwriting Serum. DeLonge has said that the band was attempting to create “nursery rhymes on steroids.” It’s an apt description. Blink tracks from the late ’90s often featured childishly offensive lyrical content and seemed to move at 2x speed. But nothing from their catalog channels that hyperactive essence better than Enema of the State. The 38-minute record, which hit your mall’s Sam Goody on June 1, 1999, is almost annoyingly infectious. In high school, I blasted it on loop via the Discman connected to the tape deck of my dad’s Mercury Sable station wagon.

“As tough and indie punk as they wanted to be, they just wrote hooks that were too damn catchy to not sing along,” said Roger Joseph Manning Jr., who played keys on Enema. “And they got famous and rich because of it.” The story of Enema of the State, however, isn’t solely one about Blink-182’s big break. It’s also, like much of the most memorable pop music from 1999, about the perfect marriage of artist and producer as well as the profound influence of MTV. And yes, the tale contains plenty of gratuitous nudity.

Let’s begin with another scatalogically-titled ’90s album. Green Day recorded Dookie in 1993, but the band was unhappy with the mix of the record. Jerry Finn, an engineer at Devonshire Sound Studios in L.A. who assisted producer Rob Cavallo, was then given a shot at mixing it. “I think they said, ‘Shit, let’s let Jerry try,’” said engineer Joe McGrath, who’s worked with Finn and Blink-182. “And off he went.” Finn’s mix helped cement the accessibly aggressive signature sound of Green Day’s major-label debut, which after its release in February 1994 became a smash hit.

“Being realistic about the music business, I thought I’d have a red-hot career for six months and then be back assisting,” Finn recalled in Bobby Owsinski’s The Mixing Engineer’s Handbook. But to Finn’s surprise, his involvement with Dookie resulted in a variety of bands seeking out his services. Over the next several years, he mixed and engineered tracks for the likes of Jawbreaker, Goo Goo Dolls, and Weezer. He also produced Rancid’s 1995 punk classic ...And Out Come the Wolves.

The Ringer’s 40 Best Singles and Albums of 1999 1999 was one of the most interesting music years ever. We’re celebrating that by definitively ranking its top songs and albums, 20 years later.

By the late ’90s, Blink-182 had begun to achieve mainstream success. Their second studio album, 1997’s Dude Ranch, included rock radio hit “Dammit,” which most memorably played during the climax of the 1998 teen movie Can’t Hardly Wait, and which, in classic Blink-182 fashion, repeats the shrugging but introspective resolution of “Well, I guess this is growing up.”

When it came time to make a follow-up to Dude Ranch, DeLonge and Hoppus fired struggling drummer Scott Raynor and replaced him with Travis Barker of the Aquabats. As for Finn, for a group looking to refine its sound, he was a natural fit. “He was involved with the cooler punk rock bands that were doing really big, produced albums,” DeLonge told Wondering Sound in 2014. “... The thing to do was to elevate the art form, and we wanted to be on par with the most elevated.”

Enema of the State, which was recorded at a handful of Southern California studios, was indeed a collection of jacked-up, nursery-rhyme-like earworms. For better and for worse, DeLonge and Hoppus wrote from the perspective of a self-loathing, immature, teenage boy who’s clueless about women. The songs, not shockingly, are laced with both clever turns of phrase and casual misogyny.

In the opening track, “Dumpweed,” DeLonge’s diagnosis of his relationship includes the observation that “I need a girl that I can train.” The chorus of “Dysentery Gary,” a lament about someone’s asshole boyfriend, ends with “girls are such a drag.” The band later gets into DeLonge’s belief in extraterrestrials (“Aliens Exist”), the lameness of frat bros and the kind of girls that they go for (“The Party Song”), and a boring couple that wants to bone (their word) and do nothing else (“Mutt”).

A reflexive and frequently rude insecurity pervades the album, but a smidgen of self-awareness can be found within. During “Don’t Leave Me,” Hoppus implores his soon-to-be ex to not “let your future be destroyed by my past.” In “What’s My Age Again?,” the prank-loving narrator can’t even focus well enough to hook up with his girlfriend. “We started making out and she took off my pants,” Hoppus sings, “but then I turned on the TV.” In 1999, he told Billboard that the song is about him being a 20-something “and acting like a jackass teenager. It is absolutely autobiographical.” Naturally, the track’s original title was “Peter Pan Complex.”

Enema has its more serious moments. “Adam’s Song,” which features Manning on piano, deals with the realities of depression. (For a short stretch in the early 2000s, it became infamous when a survivor of the Columbine High School massacre reportedly took his own life while listening to the track on repeat. Hoppus later called it “an anti-suicide song.”) Another melancholy tune was at least in part the product of Finn attending a Blink-182 concert and hearing from fans that they liked when the band sang about disintegrating relationships. “I asked Mark to write another breakup song,” Finn told MTV. “He came back the next day with ‘Going Away to College.’”

Finn was equipped, maybe better than anyone, to deal with Blink’s adolescent shtick. “A pretty typical day would involve multiple takes for one part of one song,” Hoppus wrote in the band’s memoir, Blink-182: Tales From Beneath Your Mom, “and then everyone would get naked and jump on Jerry.” Said the producer to EW: “I saw them naked more than I ever care to see anyone naked. In the mastering studio—pretty much anywhere.”

For Blink-182, learning to strike the right balance of pop and punk was a challenge. When Finn brought him in to record, Manning remembers the band being welcoming but skeptical. After he played them a melody that he’d been experimenting with, Hoppus called it “fucking awesome.” But then the bassist said, “Dude, here’s the deal …” and put his hand—sticking straight up—on the top of his own head. Manning didn’t realize it right away, but Hoppus was making the shape of a mohawk. “All the guys at our shows that have this goin’ on, when they hear that keyboard part, the hand’s gonna fall over,” he explained. “... And for that reason I don’t know if we should use it.” That became a running joke between the trio and Manning, who has continued to guest on Blink albums. “They welcomed all my ideas and they were super supportive and that’s why it was so much fun working with them,” he said. “But at the end of the day, if the mohawk goes limp, they may say, ‘It’s not right for us.’”

Enema of the State’s mixer had one goal: “Make it sound as aggressive as possible,” said Tom Lord-Alge, who at the same time was mixing songs for Santana’s Supernatural. “You don’t want to overthink it. You’re trying to capture a moment.” The band’s approach to their new album’s cover was similarly straightforward. Like the eternal teens that they were, Blink hired Janine Lindemulder to pose for a portrait as a sexy nurse. In David Goldman’s now iconic photograph, the porn star is wearing one blue latex glove. That sartorial choice only makes sense if you know one of the record’s working titles: Turn Your Head and Cough.

In 1999, MTV’s Total Request Live was a phenomenon. More than 850,000 people, the vast majority of them probably kids, tuned in every afternoon to see the latest videos by young pop stars. In the spring, “What’s My Age Again?” was released as a single. Around the time record stores began stocking Enema of the State, the video reached TRL, introducing the band to millions of teenagers. Publicly, the trio reacted to their exploding fame as maturely as their new audience might’ve. During a visit to the show’s Times Square studio, the band staged a BMX race. Hoppus did his loop around the set wearing nothing but goggles. “I have yet to interview a naked man,” host Carson Daly said as he handed him a towel. “I am not gonna start right now.”

Late that summer, after the members of Blink-182 cameoed (with Crystal the Monkey) as viewers of Jim’s primitively live-streamed first sexual experience in teen comedy American Pie, they once again teamed up with Siega. Their second video together would be for “All the Small Things,” a radio-friendly Enema throw-in that DeLonge wrote to please MCA, the band’s record label. (The catchy love song was first called “Babycakes-Buttermuffin.”)

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Back then, boy bands were the dominant musical force, and in a way Blink-182 were nothing if not a more profane, slightly different sounding boy band. It’d be fun, Siega figured, to send up those wildly popular artists. “I just thought it was a good way to take advantage of that sort of pop culture phenomenon of music videos at the time,” said the prolific TV producer and director, who just shot the pilot for Batwoman. “Why not just lean into those other massive other hits that were happening?”

There’s an episode of MTV’s Making the Video—in the late ’90s and early ’00s, music videos were big enough to dedicate an entire series to how they were made—centering on “All the Small Things.” On the show, Siega recalled, “the guys and I did a little reenactment of the phone call when I called them and pitched the idea to them. Because when I told Mark the idea I remember the hesitation of almost like, ‘Hmm, I don’t know.’ But somewhere in their private conversations they took a leap and went with it.”

Filmed at Van Nuys Airport and Santa Monica State Beach, the video mocked tropes made famous by the Backstreet Boys, ’NSync, 98 Degrees, Britney Spears, and Christina Aguilera. There are choreographed dance routines in multiple locations, including in front of a private jet, crying fans, and plenty of slow-motion shots. At various points, DeLonge puts in a set of hillbilly false teeth, Hoppus strips down to his underwear, and Barker rolls around on the sand with a bikini model.

The way Siega saw it, the parody wasn’t a “fuck you” from Blink-182 to boy bands. After all, thanks to MTV, the two shared fans. “In some ways, they’re poking fun at themselves,” Siega said. “Because they were a part of that. They were on TRL as well and running around naked. I think they just knew how to express themselves in a way that never came across as, ‘We’re bigger and better than those guys.’”

While Blink-182 were never as famous as the Backstreet Boys or ’NSync, they soon became pop stars themselves. In September, the “All the Small Things” video premiered. After it spent months on the countdown, TRL retired the clip. The song, which made it to no. 6 on the Hot 100, remains the band’s highest-charting hit.

In early December, after Enema of the State had gone multi-platinum, the band appeared at the Billboard Music Awards. Obviously they showed up naked.

About all that gratuitous nudity …

Being expected to disrobe at every public appearance began to gnaw at Blink-182. Seeing themselves portrayed, as DeLonge once put it, as an “erotic boy band” was jarring. Their willingness to act out for the cameras also led to other rock stars taking shots at the trio. “In America, you can fall into a relationship with MTV of needing them,” Trent Reznor told Kerrang! in 1999, “and then you wind up in your underpants introducing your new video.” While Blink seemed to view that line of criticism as pretentious—“Being thought of as a joke band is better than being thought of as an ‘art band’ or a ‘heavy band,’” Hoppus fired back at Reznor in the British magazine back then—their TV-fueled fame took a toll on the band.

“We were coming from the punk scene, but the label fashioned a whole thing around us that we didn’t even understand; we were just kinda caught up in it,” DeLonge said in 2014, “so it took us a little bit to dig out of that and come back to who we really were.”

After Enema of the State, Blink-182 didn’t instantly grow up. But despite naming their 2001 album Take Off Your Pants and Jacket, the band gradually grew less interested in acting like jackass teenagers. Their next album, the third that they recorded with Finn, didn’t even have a dirty pun for a title. It was simply called Blink-182. “We didn’t just say, ‘Hey, let’s make a mature record!’” DeLonge told The Washington Post in 2004. “We don’t think like that. We are multidimensional people, and we’re not running naked and happy all the time, contrary probably to what most people thought about this band a good 10 or 12 years ago when we started.”

Alas, in 2005, tension between DeLonge and the other two members of Blink-182 over the direction of the group led to the band breaking up. Fittingly, MTV correspondent SuChin Pak announced what a press release described as Blink’s “indefinite hiatus” on TRL.

For the fractured trio, the next several years were extraordinarily traumatic. In the summer of 2008, Finn suffered a massive brain hemorrhage. On August 21 of that year, the man that Hoppus once called “the anchor for everything” Blink-182 recorded, died at 39. “Every day I scratch my head and go, ‘OK, why did he have to graduate from the planet so damn early?’” Manning said of Finn, whose final finished work, Morrissey’s Years of Refusal, came out in February 2009. “One day he’s here, one day he’s gone. It makes no sense.” To this day, engineers and producers ask him about working with Finn. “You can turn down any of these records that he worked on very, very soft and they’re like, still exploding out of your MacBook speakers,” Manning added. “And that doesn’t just happen. You have to know what you’re doing and going for.”

Less than a month after Finn’s death, Barker survived a plane crash that killed four people and caused burns covering 65 percent of his body. The accident led to him facing 27 surgeries in addition to excruciating mental and physical pain.

In 2009, DeLonge, Hoppus, and the recovering Barker reunited. In 2015, they went through a bitter, second breakup. This spring, the band—absent DeLonge, who’s turned his obsession with aliens into two TV series—announced a tour to celebrate the 20th anniversary of Enema of the State. As silly and inappropriate as it can be, the still-infectious album has been a primer for countless young pop-punk bands.

Early this month, I went to a Blink-182 concert at an outdoor amphitheater in Northern Virginia. (Through a publicist, the group declined to be interviewed for this article.) I was initially surprised to find that the place wasn’t overrun with teens. Then I realized that the trio’s teenage fans are, like me, currently in their 30s.

After opener Lil Wayne—yes, Lil Wayne—cut his set short, Blink took to the stage to Jules’s version of Ezekiel 25:17 from Pulp Fiction and kicked right into Enema of the State. With Barker on drums and Alkaline Trio guitarist Matt Skiba sharing vocal duties with Hoppus, the group played the record in full. Aside from spots of banter—the all-black-clad Hoppus made a crack about Alvin and the Chipmunks covering “All the Small Things” and after playing Enema of the State in its entirety, he “joked” that they’d perform more songs because they were contractually obligated to do so—the band didn’t much go off script.

I mostly didn’t mind the lack of spontaneity. Hoppus is 47, Barker is 43. Watching the band try to repeat the transgressiveness of their 20s would’ve been a painfully lame experience. Yet even as I was enjoying the nostalgia fest, I couldn’t help but be reminded that the Blink-182 of 1999 was gone. Barker may have played the drums shirtless, but no one came close to getting naked.