“What drew me into hip-hop,” said Tariq Trotter, widely known as Black Thought of the legendary Roots crew, “was that it was, you know, spoken in a language that, you know, people who were 30, 40, 50 years old didn’t understand.”

Trotter was in conversation with NPR’s Tonya Mosely as the two discussed Trotter’s new memoir, The Upcycled Self. The book charts his path both as an artist and an individual; it includes heavy details about his life, including the murders of both his parents, as well a fire he set in his house at the age of six. Trotter, now 52, is clear about his personal maturation process, and how the culture of hip-hop has grown as well.

Trotter appreciates the many subgenres within hip-hop, even if he doesn’t understand them; and that’s because he’s not supposed to. The popular sound of today, drill music, isn’t made for people his age. Trotter, who will be in discussion with Jelani Cobb at San Francisco’s City Arts & Lectures on Saturday, Feb. 24, concluded his point by telling Mosely, “We’ve become our parents and grandparents at this point, you know?”

Andre 3000 attends the GQ Men of the Year Party 2023 VIP dinner at Chateau Marmont on Nov. 16, 2023 in Los Angeles. (Emma McIntyre/Getty Images)

As the celebration of what’s widely regarded as hip-hop’s 50th anniversary year comes to an end, I’m waiting for someone to make one of those montages that plays at the end of a movie. You know, where they show a sepia-colored portrait of each prominent character, overlaid with a couple lines about what eventually came of their lives.

When the cheesy music starts, the first image could be of OutKast, the famed Atlanta duo who showed the world that you can rhyme about Cadillacs and spaceships in the same breath. André 3000, who made his mark at the 1995 Source Awards (“the south got something to say”), is now a world-traveling flutist who dropped a full-length jazz album. Meanwhile, his former partner in rhyme, Big Boi, a renowned lyricist and actor who played the role of a dope dealer named Marcus in the hit movie ATL, has become an owler.

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Members of the collective that birthed OutKast, the Dungeon Family, have also gone on to notable things. Just a few years after a controversial interview with the NRA, and forming an odd-couple partnership with Senator Bernie Sanders during his 2020 presidential run, lyricist Killer Mike dropped Michael, one of the most critically acclaimed albums of the year. Even at the big age of 48, folks can still rap.

Killer Mike performing in Atlanta in 2017. (David A. Smith/Getty Images)

Speaking of old heads from Atlanta who can still gas a track: Ludacris has entered the chat. In addition to co-starring in the Christmas film Dashing Through The Snow, creating a charming children’s show called Karma’s World, and doing commercials for State Farm Insurance, at age 46 Luda is reportedly working on an album for 2024. (He still has bars.)

But not everyone is doing well with maturation. Again in Atlanta, rapper T.I.’s life has become a bit of a walking reality show. Despite his large vocabulary and investment in real estate properties, T.I., who at the age of 43 recently announced an impending double album and subsequent retirement from rap, has been the butt of jokes about family issues. Most recently, the King of the South had to deal with a recorded altercation with his son.

[aside postID='arts_13923938']Speaking of hip-hop icons and domestic disputes: Diddy.

After changing his name again, this time to “Brother Love,” and dropping an album titled The Love Album: Off the Grid, it’s become extremely apparent that 54 year-old Diddy, real name Sean Combs, is the polar opposite of love. Just days after being sued by musician and former girlfriend Cassie for trafficking, rape, assault and more, Combs settled the case out of court, expeditiously. A few days later, Combs, who recently stepped down as Chairman of Revolt TV, was served with additional lawsuits from different women who alleged similar crimes. More money, more problems.

On the topic of people involved in the mid-’90s East Coast / West Coast beef and the law: Duane “Keffe D” Davis is now in prison for charges related to the murder of Tupac Shakur after his arrest earlier this fall. Just a few months later, in an unrelated but relevant story, Tupac Shakur’s name was immortalized during a street naming ceremony in the city he got his game from, Oakland.

The sign for ‘Tupac Shakur Way’ is unveiled during a renaming ceremony in Oakland, Calif., on Nov. 3, 2023. (Beth LaBerge/KQED)

Late last year, the City of Oakland also unveiled a street sign recognizing 57 year-old Too Short’s contributions to the culture in front of his alma mater, Fremont High School. Additionally, while dropping an album, releasing a cookbook, and selling enough liquor to sink a ship, 56 year-old entrepreneur E-40 got a part of Magazine Street in Vallejo named in his honor.

Staying in the Bay, the Hieroglyphics crew’s Souls of Mischief, who three decades ago famously predicted that they’d be chillin’ until the clock strikes infinity, are doing a lot more than just chillin’. They initially set out to do 93 shows this year to celebrate the 30th anniversary of their song “93 ’Til Infinity.” As of today, they’ve done 117 shows across multiple continents, and they’ve also recorded new verses over the “93 ’Til Infinity” instrumental.

Another member of the class of ’93 from Oakland, 52 year-old Boots Riley, has been on a run. His 2023 TV series about a giant Black man from East Oakland, I’m A Virgo, has been nominated for multiple awards. Behind the scenes, Boots has continued to point out injustices in our society, with a focus on the predatory nature of capitalism.

A person in a very tall hat speaks in to a set of microphones at a podium in an outdoor setting. — Boots Riley speaks at the 2023 Writers Guild Of America Strike: Rally And March at Pan Pacific Park on June 21, 2023 in Los Angeles. (Momodu Mansaray/Getty Images)

On the subject of early ’90s West Coast MCs who once used their music to give the middle finger to Uncle Sam before turning to film, there’s Ice Cube. The good news is that Cube, the 54 year-old founder of the Big3 basketball league, is still making music and movies, just as he did three decades ago. The bad news? He’s also giving tours of the hood to conservative white folks. Then again, that’s kind of what mainstream “gangsta rappers” have always done, right?

Politics hasn’t always been the most welcoming arena for hip-hop artists, but just this past week, 53 year-old Queen Latifah received praise from President Joe Biden as she became the first female rap artist to receive the prestigious Kennedy Center Honor.

While we’re awarding artists who’ve done the work and then some, let’s talk about the ever-influential Missy Elliott, who at the age of 52 was inducted into the Rock & Roll Hall of Fame this year. (68 year-old DJ Kool Herc, a founding father of hip-hop, joined her as a 2023 inductee.)

A close-up of a Black woman's face with colorful eyeliner, as she sings into a microphone — Lauryn Hill has written about feeling pressured to choose between her career and motherhood. (Paul Hawthorne/Getty Images)

Despite the revelation that Fugees member Pras was once a federal agent, that didn’t stop 48 year-old Lauryn Hill and the crew from reuniting for a few shows around the country, including one last month in Oakland.

There are veteran artists doing completely unforeseen things, like Redman (age 53) becoming a licensed skydiver or Twista (age 50) teaching firearm safety and rapping to the sound of bullets flying at a shooting range. And then there are artists continuing what they’ve been doing, just at a higher level. Method Man is a certified actor who still periodically drops a verse here and there, and at the age of 52 moonlights as a sex symbol. Lil Kim, who at 49 has her own claim as a sex symbol, just penned a memoir that’s set to release next year. Texas OG Bun B, a 50 year-old who knows his way around the kitchen, has opened a restaurant called Trill Burgers. The ever-fashionable megaproducer Pharrell, who doesn’t age despite government records showing he’s 50, is now designing for Louis Vuitton. And 53 year-old MC Lyte, whose voice dropped rock-heavy flows when hip-hop was in its nascent form and has since gone on to host award shows, is now using her voice to talk to the next generation of Black girls interested in coding.

Rakim performs at Blue Note Jazz Festival on Sunday, July 30, 2023. (Eric Arnold)

Let’s take a second to pause, and acknowledge the many hip-hop artists who’ve died at a young age due to poor health. And follow that by celebrating and supporting the legends who are living, like Scarface (53) and Rakim (55), who both recently received healthcare benefits and financial support from the Paid in Full Foundation. Health concerns for our aging icons are also part of the reason folks’ ears perked up when 52 year-old Snoop Dogg posted on social media that he’s “done with smoke.” And, because he’s Snoop, we weren’t surprised when the news turned out to be a commercial for a smoke-free fire pit.

[aside postID='arts_13934874']In this 50th year of hip-hop, we’re grateful to see the resolution of feuds between artists. Ma$e (48) and Cam’ron (47) reunited and created “It Is What It Is,” a talk show that’s full of laughs and insight on current events. North Carolina’s hip-hop duo Little Brother recently released a documentary film, May the Lord Watch: The Little Brother Story, highlighting their friendship’s trajectory. And on the more romantic side of reunions, Nelly and Ashanti got back together, and are expecting their first child.

That’s a good segue to the news that at the age of 48, the first woman to go platinum as a rap artist, Da Brat, just gave birth to a baby boy.

You never thought that hip-hop would take it this far.

Juvenile performs with Mannie Fresh and an all-star band at the NPR offices in a Tiny Desk Concert. (Catie Dull/NPR)

Neither could we have imagined that at the age 45, Trina, Ms. “Whoop-whoop, pull over, that ass is too fat,” would be performing at the offices of National Public Radio. Nor Mr. Back That Azz Up, a.k.a. Juvenile (48), for that matter. But yes, both happened this year.

A half-century since hip-hop started and there are many reasons to rejoice, despite some of the unsavory news. As fans, we’re appreciative that the catalogs of Young Jeezy and De La Soul are now on streaming sites. And we’re equally appreciative that there’s new music from the likes of J.Cole, Lil Wayne and Nas, who at age 50, has dropped multiple award-winning albums in the past five years and had a resurrection unlike anyone else in the game—with the possible exception of Black Thought.

When Tariq Trotter isn’t rocking as a part of the house band for Late Night with Jimmy Fallon, he’s writing off-Broadway plays and acting in films. But don’t think for a second he can’t spit a scorching freestyle, too. He’s dropped verses on projects with younger rappers that show he hasn’t lost a step. And he’s put out a few highly acclaimed projects over the past couple years — arguably some of his best work — with music that speaks to middle-aged hip-hop heads.

Black Thought plays Hiero Day in Oakland on Monday, September 3, 2018. (Estefany Gonzalez )

During his interview with NPR, Black Thought talked about maturing, and that he feels more comfortable sharing more intimate details of his life. “As artists, there’s a dance, there’s a negotiation that takes place,” Trotter told Mosely. “But it’s the sort of thing that I was holding on to for the right moment — you know what I mean? For when it made the most sense. And that’s right now.”

And that right there is all the more reason to appreciate the aging process.

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Black Thought appears in discussion with Jelani Cobb on Saturday, Feb. 24, at the Sydney Goldstein Theatre in San Francisco as part of City Arts & Lectures. Details and ticket info here.

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