Exactly when did LL Cool J stop being relevant? How do you pinpoint it when the man has fallen off and bounced back so many times? It's indisputable that the man has officially fallen the fuck off; but when did it happen? Perhaps a brief look back will aid us in locating this moment.

First Epoch (or, Bigger, but Perhaps Not Deffer)

With his 1985 debut, Radio, LL became Def Jam's first artist, a scrappy teen from Queens who talked shit better than most. Rick Rubin provided sparse, hard-hitting production, and hardcore raps like "Rock the Bells" were plentiful; the sappy lover's rap "I Want You," however, foreshadowed the future lameness that would ultimately become his trademark.

His 1987 follow-up, Bigger and Deffer, was a huge hit, though critics and fans regarded it dubiously; even though "I'm Bad" was LL at his cocky best, BAD is best remembered for "I Need Love," which opened the door for J.Lo/Ja Rule collabos and—gasp—possibly even emo rap. Perhaps sensing this, the hiphop nation began to brand LL a sellout. LL's third, Walking with a Panther (1989), hit big with "Going Back to Cali," the infidelity ode "Big Ole Butt," and one of his most arrogant moments, "I'm That Type of Guy." The hardcore hiphop took a back seat, as LL was now focused on the ladies; while rocking at the Apollo, LL was booed mercilessly by his former fans. This marked the first time his cred bottomed out; it's a bad look when Kool Moe Dee thinks he can dis you with impunity. But if you had the cassette version of WWAP (and in '89, why wouldn't you?), you heard LL's first rebuttal "Jack the Ripper," which hinted at what was next.

Second Epoch (or, Technically, His Grandmother Told Him to Do It)

Mama Said Knock You Out (1990) was the stunning comeback (wait, don't call it that) many doubted LL had in him. Besides the title track, which still gets me pumped, the disc had Marley Marl's remix of "Jingling Baby," one of rap's best party tracks. It wouldn't take long, however, for Cool J to fuck up again with the dismal, back-to-hardcore-LL 14 Shots to the Dome... why would you ever name a song "Pink Cookies in a Plastic Bag Getting Crushed by Buildings"? With the release of Dome, LL got punished for doing what everybody else on the East Coast did in '93: emulating the West Coast. The Future of The Funk officially catches his first brick (Dome only went gold).

Third Epoch (or, Mr. Smith Goes Platinum)

Faced with the disappointing sales of his last LP, LL gets sappy as all hell on 1995's Mr. Smith, doing ballads with Boyz II Men, and getting out his lip gloss on "Doin' It" and "Loungin"—and selling a couple million in the process. He scared us all silly by finally revealing what his shiny, gargantuan head looks like, then tossed the streets a bone with his "I Shot Ya (Remix)," a giddily gutter posse cut with relevant rappers like Fat Joe, Prodigy, and Foxy Brown; while he went the better part of his career with not one guest on his albums, he'd eventually overdo the collaborations. After Mr. Smith, LL released All World, a greatest-hits comp; a sure sign that his actual rap career had ended. Every release that followed seemed to be an attempt to perfect a signature aggressive mediocrity. When Uncle L started calling himself the Greatest of All Time, even Russell Simmons had to chuckle.

After this thorough and thoughtful analysis, it becomes clear that LL's greatest crime is that, musically, he's never grown beyond the egomaniacal, horny teen he's portrayed on wax for 20 years. No amount of muscle mass, lip licking, or plastic surgery (LL now resembles an animĂ© version of himself) can keep you relevant when it's your time to be put out to pasture (AKA Queen Latifah movies). LL Cool J's newest album, Todd Smith, features a "hot" rapper or R&B singer on every track save for one, and is possibly his least interesting LP—which is saying a lot. "I wanna max out everything that's inside of me," said LL in a recent MTV interview. "I want to die empty." Until then, could you at least stop rapping?

hiphop@thestranger.com