Oops, they did it again: The 15 best songs to hit the Billboard Hot 100 in 2000

Perusing the lists of hit songs from years gone by can be an illuminating experience—not just to be reminded of what was popular at a certain point in time, but also to see how your own relationship to the pop culture of that era is or isn’t reflected in your views now. That’s a fancy way of saying, “We all used to think some terrible garbage was awesome, and we all have subsequently come to realize that some of what we thought was garbage then has now become acceptable, or even great.” It can be hard to separate the rosy hues of nostalgia from critical assessment of music with which you’re very familiar; in fact, let’s go ahead and say it’s impossible. Better to acknowledge the bond, and see what else is there on top of your affection.

Which brings us to the year 2000. It’s almost startling, looking over the Billboard Hot 100 charts of the year, to realize how many hits from those 12 months have endured in the bedrock of American pop culture. “Smooth,” by Santana with Rob Thomas, is going to be a staple of easy-listening radio and playlists for decades, for good or ill. (Mostly ill.) Christina Aguilera’s “What A Girl Wants” became a movie title, but mostly it became a go-to song to play snippets of over YA film and television to signify a moment of empowerment. And Coldplay’s “Yellow” will likely live on via mixes made for high school kids, by other kids who have crushes on those kids, until the end of time.

What’s most striking is how profoundly rock music had already diminished in the tastes of mainstream Americans by the turn of the millennium. (Sorry, “Willennium.”) Unless you’re a fan of the cringe-inducing warblings of Creed or the nu-metal and rap-rock stylings of Limp Bizkit, Kid Rock, and their ilk, there’s not much to choose from, save for the gentler AOR sounds of groups like Third Eye Blind and Matchbox Twenty, a sound perhaps best captured by unexpected No. 1-charting “Absolutely (Story Of A Girl)“ by one-hit wonders Nine Days. America’s youth had moved on, embracing R&B and hip-hop, while simultaneously ushering in another wave of boy-band mania. When unstoppable ’90s juggernaut Pearl Jam is struggling to crack the top 50 (plaintive ballad “Nothing As It Seems” peaked at No. 49), you know the alt-rock heyday is gone.

But in its place was a fascinating replacement. Not since the Brill Building days of the early 1960s, when corporate offices full of songwriters crafted hits for fresh-faced girl groups and teen idols, had the Billboard charts been so thoroughly saturated by artists whose songs were written by someone else. This was a trend that would only intensify throughout the 21st century, but in 2000 it was still a new development, with in-demand producers no longer just recording the hits, but writing or co-writing them with the fervor of a thousand Phil Spectors. Pop stars would often hire the most expensive talent, knowing they were primed to deliver the best prefab pop hits engineered to climb the pop charts. This method was eventually codified by the Swedish pop maestro Max Martin, who would go on to develop a literal formula for pop hits and an army of employees working to do the same, with his proteges shaping the next two decades of the pop-music landscape. But at the time, Martin was busy churning out his first No. 1s, following up 1998’s “…Baby One More Time” for Britney Spears by delivering ’N SYNC their 2000 hit, “It’s Gonna Be Me.” (Which got more than a few votes in this process.)

The only criteria for consideration in this Power Hour was that a song had to have charted on the U.S. Hot 100 charts between January 1 and December 31, 2000 (and only one entry per artist—sorry, Destiny’s Child). So it’s not surprising to see that a number of winners are exactly the sort of meticulously crafted formulaic pop ditties that bestrode American pop culture like a colossus. Yet following the recipe doesn’t insure victory; the great thing about pop is that success still comes down to that vague and indefinable “it” factor that makes something so hooky and compelling, it demands attention. (This can be used to evil ends, as well: See the entire career of Black Eyed Peas.) So enjoy this Power Hour composed of the finest hits of 2000, 60 minutes’ worth of songs that received the most votes for inclusion because they just refuse to stop rattling around our brains, in the best possible way. Some may be the expected presences (i.e., anything Destiny’s Child so much as glanced at), some may be surprises (hello there, Sisqó!), but they all share one quality: They’re not just what sounded good to America in 2000, but what still sounds good today. [The Off The Charts edition—the best songs that didn’t make the Hot 100 in 2000—will be coming in a few weeks.]

“Big Pimpin,’” Jay-Z

Jay-Z’s hit was so omnipresent in 2000, you even had Conan O’Brien covering it in the promos for that year’s VMA awards. But more than just being a wildly popular tune, it has endured as one of Hova’s most memorable tracks, and it’s not hard to see why: With its Caribbean-flavored rhythms and instrumentation, the track creates instant song-of-the-summer vibes, the kind of jam anyone can enjoy blasting from their speakers on a lazy July day. And while Jay-Z himself may regret the vacuous party-animal lyrics in hindsight, they’re delivered with his signature flawless flow, his monster single introducing millions more to his talent. [Alex McLevy]

“I Try,” Macy Gray [Patrick]

Even among the other songs included on 2000’s diverse Hot 100 chart, there was nothing else quite like this second single off Macy Gray’s debut album, On How Life Is. The soulful R&B track made Gray a star, her signature rasp on full display as she wailed out, “I’m dreaming of you, babe.” Gray has gone on to release nine more studio albums, but has yet to top “I Try,” which lasted 89 weeks on the Billboard 200. At the height of its popularity, the song played during Michael J. Fox’s goodbye on Spin City. Since then, it was sung by Ed Helms on a 2010 episode of The Office, and most recently was used in a 2018 episode of The Last Man On Earth. If Gray really is trying to say goodbye, it’s not working. [Patrick Gomez]

“Oops… I Did It Again”, Britney Spears

When it was first released, the title track from Britney Spears’ second album seemed like exactly the kind of disposable earworm that would burrow into your brain for a few weeks, then be forgotten as soon as her fifteen minutes of fame were up. But just as the pop star has managed to continue a surprisingly enduring career of success despite an admittedly limited vocal capability, so too has her ode to breaking hearts continued to be a successful pop staple, proving that even the frothiest of bubblegum has a winning formula—namely, hire the best producers money can buy. [Alex McLevy]

“All The Small Things,” Blink-182

You can’t say that the San Diego skate punk trio known as Blink-I82 wasn’t persistent: The band didn’t really break out until album number four, Enema Of The State, aided by the ubiquitous “All The Small Things,” which reached No. 6 on the Billboard Hot 100, a band career high point. Written as a love song by singer/guitarist Tom Delonge for his then-girlfriend/now-ex-wife Jennifer Jenkins (who reportedly really did leave him “roses by the stairs”), the song once more sailed pop-punk into the mainstream, its sing-songy infectiousness transcending all genres. Those “nananana”s in the chorus, a nod by Delonge to punk godfathers the Ramones, certainly helped, as did a snarky video making fun of boy bands. The inescapable hit soon appeared on soundtracks from Charlie’s Angels to The Simpsons. [Gwen Ihnat]

“Independent Woman, Pt. 1,” Destiny’s Child

It was a marketing strategy so straightforward that it damn-near planned itself: Pair the year’s biggest female-led blockbuster, Charlie’s Angels, with one of the most globally revered girl groups of the time, Destiny’s Child. “Independent Women, Pt. 1” was such an effective leading track that at the time, culture analysts heralded the song for stoking interest in the film’s release the same way that Janet Jackson’s “Doesn’t Really Matter” did for Nutty Professor II: The Klumps that same year, both in heavy airplay and strategy. Apart from the popcorn flick that inspired it, the song quickly turned into a banner-waving theme song for female empowerment, despite the weighty movie references. [Shannon Miller]

“Ms. Jackson,” Outkast

“Ms. Jackson” is the one small step/one giant leap between Outkast’s days as bestselling ATLiens keeping the spirit of P-Funk alive and their elevation to hip-hop gods on the playlist of any wedding DJ worth hiring. The apologetic cut is more of a “passing a joint after the reception” type of song, but it does toss multiple interpolations of “The Bridal Chorus” into its woozy psychedelia, a singular jumble where dog barks, rolling thunder, slap bass, and backward bongos subtract nothing from the emotional heft. Big Boi and André 3000 bob and weave around that reverberating beat, in verses that never settle on any one particular flow for too long, but match an eclecticism that’s meant to last forever. (Forever ever Forever ever) [Erik Adams]

“Stan,” Eminem feat. Dido

A song so prescient that it came to define the kind of maniacal fandom it depicts, “Stan” helped elevate Eminem from foul-mouthed curiosity to critical darling and Grammy headliner, and rightly so. The song’s epistolary structure and spiraling narrative still feel fresh two decades on, and its title character is sketched and performed with nuance, his mania slowly puncturing through his pleasantries. Artists on the rise often create works that reckon with the pressures of fame, but what “Stan” does that most don’t is shift the emphasis outward. Eminem isn’t concerned about what fame’s doing to him, but what his work is doing to other people. The looming question, one that’s become even more urgent in the age of social media, is what responsibility celebrities are supposed to take for their fans. [Randall Colburn]

“Bye Bye Bye,” ’N SYNC

“Bye Bye Bye” marked a huge turning point for boy band ’N SYNC (or *NSYNC or NSYNC, listener’s choice). On the band’s third release No Strings Attached (following their 1998 debut and a Christmas album), ’N SYNC appeared to be making a statement about leaving behind their old label, RCA, and their former manager Lou Pearlman, in the form of a relationship breakup song. “Bye Bye Bye” was a true mission statement, displaying a futuristic ferocity their previous vapid hits like “I Want You Back” could only dream of. The video played up the breaking-free-from-puppetry theme; even the choreography was more athletic and aggressive. The commanding rebrand led the song to No. 4 on Billboard Hot 100; although ’N SYNC only put out one more record after Strings, “Bye Bye Bye” stands as the band’s pinnacle: rebellion scored to a dance-ready backbeat. [Gwen Ihnat]

“Party Up (Up In Here),” DMX

Twenty years after its release, DMX’s anthemic “Party Up” is still one of the most efficient shots of energy to any gathering (that is, when gatherings were still a thing). The second release off of the rapper’s third album, …And Then There Was X, was not only a charting smash, but a pervasive pop culture moment: In 2000 alone, the song appeared on the Gone In 60 Seconds soundtrack, Dave Chappelle’s HBO special Killin’ Them Softly, the NBA championships, Daria, and in just about anything else that wanted to ride its wave. Cultural juggernauts maintain its abiding legacy to this day, including Lin-Manuel Miranda, who referenced the high-octane hit in Hamilton. [Shannon Miller]

“Music,” Madonna

In an effort to stay atop her pop music throne, Madonna greeted the millennium with a re-energized electronic sound, ushering in her “Femme-pire” era (to borrow a term from Drag Race’s latest Rusical). With a tip of the cowboy hat, Madge had reinvented herself yet again in the style of glammed-up Americana, the new aesthetic crystallized by inescapable single “Music” and its accompanying video. Co-written and produced by French artist Mirwais, the track is structured around a futuristic, glitched-out bass groove and some digitized vocals. Given country and disco’s more recent resurgences in mainstream pop, Madonna’s “Music” feels as fresh as ever, even if the video’s Debi Mazar and Sacha Baron Cohen-as-Ali G cameos make it distinctly a product of 2000. [Cameron Scheetz]

“Try Again,” Aaliyah

A post-Matrix reimagining of the Bard’s star-crossed lovers, the Jet Li-starring Romeo Must Die came and went in the spring of 2000, despite featuring Aaliyah’s onscreen debut. Where the film really made an impact was the Billboard charts, with Aaliyah’s soundtrack-leading “Try Again” becoming her first and only number-one hit. Unlike the sleepy action flick, “Try Again” gets the blood pumping, fueled by a hypnotic stop-and-start beat from Timbaland that fuses the sounds of house music with R&B. Aaliyah’s arresting vocals—hardly above a whisper—slink sensually across the track’s syncopated rhythm. With its success, “Try Again” pointed to a bright future for both artists, if only Aaliyah’s wasn’t cut tragically short. [Cameron Scheetz]

“Untitled,” D’Angelo

The sexiest song of this year (and quite possibly any other). A slow jam that needed no title, no proper ending, and no wardrobe for the video. An homage in regal shades of purple, from the supple groove and the roomy production to the falsetto ad-libs and the almost-one-man-band recording session. (That’s Raphael Saadiq dropping by Electric Lady Studios to do the Prince-does-Hendrix blues licks.) How does it feel Like that leave-’em-wanting-more outro (they ran out of tape; Saadiq said, “Just leave it like that”) could build and build and build until there’s nothing left but you and all those overdubbed D’Angelos, hanging in space and horny as hell. [Erik Adams]

“Thong Song,” Sisqó

The worst thing about “Thong Song” is all the hacky jokes about it. (Yes, yes, “dump” is a word with multiple meanings. We get it.) Look past the absurdity of the overall concept, and you’ve got a wonderfully strange and deceptively simple hit, built around an infectious looping beat, Sisqó’s theatrical belting, and strings performed by the same musicians who did the score for Star Wars: Episode I—The Phantom Menace. That string arrangement was tweaked until it was just different enough from “Eleanor Rigby” that Sisqó didn’t have to pay royalties to Michael Jackson, who owned the rights to the Beatles catalog at the time. But the strangest behind-the-scenes detail is that Sisqó claims he didn’t know what a thong was until shortly before the recording of “Thong Song,” which is surprising considering the passion with which he evangelizes for the humble strip of material in the song’s final, go-for-broke minute. No man has ever been as blown away by the top of a woman’s underwear as Sisqó is in “Thong Song,” and honestly Bless him for it. [Katie Rife]

“Otherside,” Red Hot Chili Peppers

“Scar Tissue” helped signal the melodic bent of Red Hot Chili Peppers’ Californication, but that wistful jam still didn’t prepare fans for the emotive grandeur of “Otherside,” a moody cut about addiction that few might’ve expected from the guys who wore socks over their dicks. (Especially if they hadn’t already heard “Under The Bridge.”) “Otherside” also benefited from its stark music video, which reimagined the oft-shirtless rapscallions inside a nightmare world influenced by German Expressionism. The shirts were back off by the time they shared a video for Californication’s title track, but the impact of “Otherside” resonates; it’s still a staple of their live shows. [Randall Colburn]

“The Next Episode,” Dr. Dre feat. Snoop Dogg, Kurupt, Nate Dogg

For a second time, Dr. Dre almost single-handedly defined the sound of West Coast hip-hop for a new generation of mainstream rap fans. While multiple tracks from The Chronic 2001 were in the running for this feature, “The Next Episode” wins because its hook is so undeniable, and so immediate, that it remains potent as ever two decades later. Snoop’s verse recaptured the rapper’s effortless early-’90s cool, and Nate Dogg’s singular vocal melody is the kind of thing you’ll find yourself singing unconsciously for the rest of your life. (And, um, Kurupt is also in there.) Or consciously, say, when you light up after a long shift: “Smoke weed every day.” [Alex McLevy]

“Country Grammar (Hot Shit),” Nelly

St. Louis is technically part of the Midwest, but Nelly’s lyrics, production, and even pronunciation align him with the Dirty South rappers who broke through in the early ’00s—if only because he doesn’t fit in anywhere else. His first single as a solo artist after departing from his hometown group the St. Lunatics, “Country Grammar” showcased Nelly’s blend of styles and talent for pop-rap earworms from the jump, adapting a timeless children’s rhyme into a breezy ode to cruising around “the ‘Lou,” showing off and having fun. The sentiment (and the hooks) proved irresistible even to coastal listeners, propelling “Country Grammar” to No. 7 on the Billboard Hot 100 and Nelly’s debut album of the same name to eight-time platinum status. [Katie Rife]