Jay-Z (Matt Winkelmeyer/Getty Images)

When I was perusing the list of new-release albums from this past Oct. 13, it dawned on me after some time that three of the artists—Wu-Tang, Camp Lo and Krayzie Bone (with his group Bone Thugs-n-Harmony)—all released albums that I absolutely loved exactly 20 years ago.

In 1997 I turned 16, obtained my driver’s license and started my first job: tutoring elementary school kids at a YMCA on the east side of Detroit. Wu-Tang Forever, Uptown Saturday Night and The Art of War served as soundtracks for that memorable and transitional year; each artist will always have enough cachet with me to allow for an honest listen of any future material.

Unsurprisingly, I wasn’t feeling any of the new projects, though I was most disappointed by the somnambulistic production and late-40s lyrical ennui (I’m looking at you, Cappadonna) on the Wu-Tang album.

The fact that my expectations were low to begin with made me wonder if beloved rap artists who add to their oeuvres well past their prime could be tarnishing their reputations. Is there something to be said about rappers getting out of the game for good while they’re ahead?

Talented musicians in other genres can make good and recognized music years past their prime: The Isley Brothers have top 40 hits across five consecutive decades, mainly because you’re never too old to sing about love, and Ronald Isley’s falsetto is like riding a slide made of melting butter into a vat of cream.

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In contrast, braggadocio is part of the fabric of hip-hop, and talking shit rings increasingly hollow the older a rapper gets. “Ante Up” might be the hardest rap track of all time, but I don’t need to hear Billy Danze and Lil’ Fame rapping about murking niggas in 2017. Anyone with college-age children shouldn’t be rapping about murking niggas.

Older rappers also have to strike a precarious balance between making music that’s fresh and music that’s good. As much as we ’90s-hip-hop fans love the classics, we don’t want a bunch of veterans making new music that sounds like lyrical-miracle-high-powered-ions-manifesting-in-your-chamber nerd rap recorded in someone’s basement on a zip disk in 1995.

We appreciate the small handful of contemporary, lyrical rappers—like Kendrick Lamar and Joey Bada$$—for paying homage to their forefathers while sounding fresh, but older rappers are constantly in a precarious position in which they risk alienating their core base and not gaining new listeners in the process.

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A very small handful of rappers actually pull off cross-generational success in the genre: LL Cool J managed to transform his image from a 17-year-old skinny battle rapper for his 1985 debut, Radio, to a chart-topping, muscle-mountain rap balladeer by the mid-1990s, making relevant records into the early 21st century while transitioning into film and television. Fat Joe has been making music since the early ’90s and managed a top 40 hit nearly a quarter-century later with 2016’s “All the Way Up.”

And, of course, there’s Jay-Z, the patron saint of hip-hop longevity, whose album releases are still considered “events” (see: sponsored by shitty phone-service providers) 21 years after his debut album.

Jay made the biggest evolution in lyrical content with 4:44, the rap album for niggas who are at the crib at 11 on Saturday nights studying the gray hairs in their beard. Considering that it’s inextricably connected to Lemonade—arguably this decade’s biggest album of any genre—4:44 was consumed by old heads as well as youngsters who’d normally consider Jay’s music geriatric rap.

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As Jay-Z might evince, though, perhaps the truest mark of hip-hop longevity is unbridled talent on the mic. People still check for a new Nas album because he’s a living legend who seems to have only improved on the mic throughout the years. By virtue of Black Thought’s top-5-GOAT-rapper status—along with Questlove’s musical genius and the diversity of live instrumentation—the Roots will always be worth checking for.

But even the most talented cats have a shelf life. If Jay does release another album, he’ll likely be on the other side of 50—where does he go after 4:44? Why did LL bother releasing a rap album in 2013 that I swear none of you reading this can even name? Considering his penchant for puerile and non-zeitgeist-appropriate topics, will Eminem’s upcoming album fly 17 years after he released the highest-selling single-disc rap album of all time?

Maybe continued output doesn’t really matter and we won’t negatively judge rappers for their largely ignored late-career albums, just as the 42,408,274 albums Prince released in the 25 or so years before his death don’t taint his legacy.

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But I would urge many, if not most, aging rappers to find some other creative or financial venue with which to fill time—there’s a whole generation of Queen Latifah and Ice Cube fans who don’t know they started out as rappers in the 1980s. Even if you aren’t making music, do like Styles P and open a juice bar or something.

If you’re a beloved ’90s rapper with some classics under your belt, promoters will come calling for you to perform that material, and people like me will buy a ticket to the show. But I’m most likely leaving the “buy” button untouched on iTunes for your new shit, along with most other people.

Consider that when you think about how much studio time costs.