Ludacris was the first Atlanta rap crossover success story of the 21st century. Outkast predates him, obviously, and three generations of crunk rappers, snappers, and trappers would succeed him. But at the turn of the century, Ludacris’s debut album, Back for the First Time, was Atlanta’s earliest foray into a whole new era of commercial hip-hop dominance.

For a rapper generally regarded as a great singles artist, with no “classic” albums to his credit, his longevity was astounding. He dropped hits clean through the 2000s: seven top-10 records, including two no. 1s (“Stand Up,” “Money Maker”), five platinum albums, and eight platinum singles. Through his label Disturbing tha Peace’s relationship with College Park rap group Playaz Circle, he basically discovered 2 Chainz, who would advance DTP’s legacy into the 2010s. From 2000 through 2006, Ludacris was hip-hop’s senior ambassador to pop culture.

More than a decade later, though, Ludacris is perhaps the least fondly recalled hitmaker of his era. Nelly had a similar run of 2000s rap crossover hits, and I think most rap fans would stand by all of them. And T.I.’s hit singles from the same decade have all held up pretty well, too, including the full-tilt sellout records he did with Justin Timberlake. Luda made great records, too — at least, I now vaguely remember them for once having sounded pretty great. He had a loud and shameless knack for Seussian riddles and vulgar puns that sounded like no other pop music that anyone, rappers or otherwise, had ever made. At the time, it was fresh.

So what is it about Ludacris’s music that seems to reek of a lapsed sell-by date? Is it the stench of pop crossover? The fact that his signature penchant for goofy over-enunciation inevitably sounds quaint now that so much Southern (and Southern-influenced) rap music is decidedly slurred and sung? Is it the misogyny (“Move Bitch,” “Ho”), which is too campy and blunt to blend in with the rest of pop culture in the 2010s? Really, it’s all of those qualities — plus the fact that his big, exuberant pop records put him sharply at odds with the now-dominant stylings of trap music — that have cursed Luda’s catalog with a pronounced obsolescence, save for a few blessed exceptions.

Below, we sort Luda’s straight-up unlistenable songs, the questionable stuff, and his undeniably great tracks in three, totally disproportionate categories.

Ludacris Songs That Have Not Aged Well at All

“Fatty Girl,” “Number One Spot,” “Get Back,” “Money Maker,” “Welcome to Atlanta,” “How Low,” “Ho,” “Blow It Out,” etc.

When’s the last time you heard “Get Back”? It isn’t even that old, in the grand scheme of Ludacris’s chart dominance; he released the song in 2004. It’s maybe my fourth-favorite Ludacris record, on the strength of his gargantuan flow over that jangly, carnivalesque beat. At least, that’s how I thought of the song back when it was still new. Now, however, I permanently associate it with the image of Tom Cruise dancing in the closing credits of Tropic Thunder, which has transformed the song into kitsch for me. Imagine my horror in having just discovered the (apparently quite popular) Sum 41 remix of “Get Back” that strips the beat away completely and replaces it with all sorts of guitar wailing and record scratching that ain’t nobody got time for.

Every popular musician scratches now and again, and it would be a disservice to an artist’s otherwise great work to harp on only their worst songs in an exceedingly ungrateful manner of nitpicking. But I would argue that Ludacris’s singles catalog is filled with songs we’d all rather not revisit, despite how cool and ubiquitous a dozen of them were at one point. The very worst of these scratches is 2001’s “Fatty Girl,” produced by the Trackmasters and featuring LL Cool J and Keith Murray doing some of the most unfortunate late-career rapping you’ll ever hear (“More nuts on your face than graffiti on the wall,” LL raps). The fact that Murray coined the term “badonkadonk” on this song is a modest consolation prize. Otherwise, “Fatty Girl” represents Ludacris’s worst quality, which so happens to also be his signature quality: the fact that he raps like a pervy uncle who loves ass almost as much as he loves puns.

Ludacris Songs That Have Aged Only Somewhat Decently, I Guess

“Stand Up,” “Area Codes,” “Splash Waterfalls,” “Diamond in the Back”

At age 15, I owned a copy of the Rush Hour 2 soundtrack, which, in retrospect, is a pretty neat time capsule of 2000s hip-hop and R&B, with songs from Ludacris, Benzino, Keith Murray, Jill Scott, and Macy Gray. The lead single from the Rush Hour 2 soundtrack was “Area Codes,” a lean, tropical song with the late Nate Dogg on the hook between Luda’s insufferably serialized puns — e.g., “Read your ho-roscope and eat some ho-rs d’oeuvres,” “Southern ho-spitality, Northern exp-ho-sure,” etc. Per the gimmicky conceit of the song, “Area Codes” naturally features Ludacris rapping a sequence of numbers for not just one, but all three verses, which is totally different and much less charming than the bit of “What These Bitches Want?” in which DMX names 46 women in the course of 12 bars. DMX was writing poetry. Ludacris was just pandering indiscriminately to various tour stops and bragging about the potency of his “big-ass sack,” a classic Ludacris double entendre.

There’s no one, prevailing quality that distinguishes this category (quaint-but-acceptable Ludacris singles) from the previous one (now-intolerable Ludacris singles), though the lyrics of the songs in this section are generally less embarrassing. These are the inoffensive dance jams and R&B-adjacent records that you might be mildly delighted to hear creep up on you in a throwback mix of songs you heard at the mall in 2003. Surely, the present decline of America’s shopping malls explains, to some extent, the concurrent deterioration of Luda’s legacy. Just a pet theory of mine.

The Only Great Ludacris Songs

“What’s Your Fantasy,” “Southern Hospitality,” “Move Bitch,” “Rollout (My Business)”

“Southern Hospitality” is right up there with “Country Grammar” and “Players’ Anthem” in the folder marked “Best Rap Beats I’ve Ever Heard In My Goddamned Life.”

Back for the First Time was produced by the strongest possible assortment of successful Southern rap producers working at the time: Organized Noize, The Neptunes, Timbaland, Jermaine Dupri, and Bangladesh. Coincidentally, Ludacris’s earliest breakout singles, “Southern Hospitality” and “What’s Your Fantasy?,” are his freshest songs. They totally hold up, they’re Atlanta rap canon, and no one can take that away from Ludacris, no matter how unkind history is to the rest of his catalog.

What’s great about the four songs listed here is that they all hit different notes in Luda’s creative range. “Rollout (My Business)” is the blackest Dr. Seuss book never written, basically. With apologies to Drake, “Move Bitch” is the hardest rap song ever made by a supposed soft rapper. “What’s Your Fantasy?” is the slickest rapping Ludacris has ever done. And to this day, I dunno that any other song has effectively succeeded “Southern Hospitality” as the official Southern black American anthem.

All of these songs dropped within a 20-month span — between September 2000 and May 2002 — which, if I were to break out the graphs and parabolas and whatnot, would indicate an acute creative peak followed by an incredibly long tail of popularity and commercial success, which didn’t peter out until with the release of Theater of the Mind and 2008’s “One More Drink” (a late-career hit so marginal that it merits no classification among Luda’s best or worst songs). By then, Ludacris was already a Fast & Furious movie and a Law & Order season finale deep into his successful relaunch as a film and TV actor.

With an incredible run of Billboard chart dominance that most so-called singles artists would understandably envy, Ludacris was once the most fuel-efficient rapper of all time, but he ran out of gas after his cameo on “All I Do Is Win” in 2010. With The Fate of the Furious due out next year, his filmography may soon mirror his previous career arc straight through the 2010s and beyond. For now, I’ll just point out that Crash and New Year’s Eve most certainly do not hold up. The rest is up for debate.