‘Never Underestimate the OG’: Richie Rich's Second Act

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n a Sunday afternoon in mid-November, LaRussell is onstage at The New Parish in Oakland, energetically hurling rhyme pyrotechnics, just days after the premiere of his NPR Tiny Desk concert.

Known for his clever lyrics, charismatic personality and nonstop production, LaRussell has refused to sign with a major label. He hosts sold-out shows at a small venue, The Pergola, built in his backyard. Staunchly independent, he’s paved his own lane in the rap game by investing in himself, his community and his culture.

His latest investment: the reintroduction of Richie Rich.

Minutes into Sunday’s show, after LaRussell warms up the crowd with violinist Michael Prince and vocalist Shanté, Rich walks out on stage.

Richie Rich’s pedigree is deep. He’s a former Def Jam signee who influenced Snoop Dogg and was friends with Tupac. He had songs on The Nutty Professor and How To Be A Player soundtracks. His 1996 album Seasoned Veteran spawned two singles on the Billboard Top 100. And his verse on the remix to the Luniz’ anthem “I Got 5 On It” provided the Town with the classic line: “Where you from? Oakland. Smokin’.”

Fittingly, at the New Parish, the artist who founded the pioneering rap group 415 enters to the beat of one of his group’s best-known songs, 1990’s “Side Show.”

Over a stripped-down instrumental on live keyboard, Rich raps bar-for-bar in his raspy, laid-back flow, crisp and clear, without any background vocals. When the chorus hits, LaRussell steps in and remixes it, pulling from the 2006 remake, “The Sideshow,” by the late Traxamillion, Too Short and Mistah FAB.

It becomes clear: this isn’t just a guest appearance of Richie Rich at a LaRussell show. No, this is two emcees, with an age gap of over 20 years, trading bars, innovating on stage and moving the crowd.

As the audience recites the lyrics, the energy builds. LaRussell and Splash Tha Kidd are on stage giggin’, jumping as they dance. After the second verse, the crowd is turned up.

Richie Rich, grounded, laughs and calmly says, “Na… that’s how you got me last time.”

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our months prior in LaRussell’s backyard, onstage at the Pergola, the energy got the best of Rich.

During a performance of the song “What We Doin!?” which features Richie Rich alongside LaRussell and an 18 year-old MC named MALACHI, Rich was in go mode. The P-Lo–produced track, full of high energy, is the type of song that makes one jump on stage — even if they know damn well they shouldn’t.

Under the scorching August sun, Rich was a few bars into his verse when the 56-year-old rapper, bouncing alongside the crowd, turned to his left. Suddenly, his knee popped. Falling to the ground, he kept rapping without missing a beat, freestyling new lyrics to communicate what’d just happened to his leg — “blew my knee actin’ out my age” — and even diagnosing it as a torn lower patella.

All of this could’ve easily become a huge setback. Instead, in a world where the elements of hip-hop have expanded to include viral moments and social media influence, the widely viewed footage of Richie Rich kicking culture while sustaining a painful injury only helped reestablish his footprint in the rap game.

I recently caught up with Rich for a long conversation at his home in the East Bay, his leg in a brace as he sat across from me. Rich is a mild-mannered person who was raised by well-to-do parents, but despite his upbringing — and lifelong issues with his knees — he ran the streets.

“I’m from up the hill, I’m not even from the flats,” says Rich, explaining his childhood and the topography of Deep East Oakland in one statement. “I went down the hill, and that shit changed me, bro,” he says.

“Them spokes that you see on that car out here?” Rich says, pointing to the gold rims of his cognac-colored 1972 Cutlass Oldsmobile. He first saw them, he explains, on a Falcon when he was 12. Little Rich ran to tell the driver how clean they were, but the light turned green and the driver pulled off. A few weeks later, Rich caught the driver at a red light and properly complemented him. The driver thanked him, and suggested he could one day have a car like that, too, before tapping the gas pedal and leaving tire treads in the intersection.

“If I live to be 90,” says Rich, fully committed to his cars, “I’ma have some gold ones and Vogues, you better know.”

Rich’s street life and hillside upbringing brought about different perspectives. He had run-ins with the law, though he often evaded them. But the culture had a grip on him.

“I was two people,” says Rich, from behind dark sunglasses. “I was Richie Rich and I was Double R.”

He elaborates: “Double R was the dude who went down the hill, Richie Rich was the dude who lived up the hill. So Richie Rich wrote ‘Do G’s Get to Go to Heaven,’” he says. “Double R wrote ‘Side Show’ and ‘Snitches and Bitches.'”

There’s always been a tug-of-war between these two sides, he says. Fortunately his dad gave him constant reassurance, and his mom gave him spiritual guidance, even if it came in the form of heavy-handed discipline.

“My mom was so strict,” Rich reflects, “that when I got caught stealing at Longs Drugs and they told me they was going to call my mom, I said, ‘Na, call the police. Don’t call my momma!'”

Once his mother found the Lord, “she brought that spirituality to us and locked us in with it,” says Rich. A sweet woman who was very hard to impress, Rich says he’d get good grades and his mother would remark, “Want to impress me? Show me that you can fly.”

When Rich signed with Def Jam, the label sent a car to take him to the airport. Misty-eyed, he reflects on his mother’s reaction. “She knocked on my door, and said, ‘There’s a limousine out front, Richie.’” Fanning out, she asked, “Can I go outside and see?”

Rich recalls her floating out the door in her trademark blue robe, sitting in the stretch limo, finally understanding that her son had made something of himself.

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ich had a conversation with his knees when he was a kid. They told him, “We’re gonna hold you down if the red and blue lights get behind you, or the dogs get to chasing you. Outside of that, don’t be attending those softball games and don’t play no three-on-threes,” he recalls.

Years later, Rich still has trouble walking in his own legacy. Almost 35 years since his 1990 debut solo album, Don’t Do It, he’s on the verge of dropping a new project titled Richard.

The album, set to release on the platform Even next month and then to all streaming services in January, features Larry June, Young JR, Jane Handcock, E-40 and V. White of The Delinquents. There’s a track where Rich pays homage to the slick players who came before him, as well as one with open critiques of current Oakland culture.

Rich has been open about his issues with the place that raised him. In January of this year the rapper made headlines for a rant he posted on social media, proclaiming that he was leaving California. “The cost of living here is going up, but the chances of living is going down,” he says in the video.

Today, he explains that Oakland losing its pro sports teams and his favorite restaurants hurts. He adds that it’s very clear that the chasm between classes is growing, and when the haves and have-nots are at odds it makes it hard to own nice things without becoming a target. (And being a known rapper from that place adds another layer.)

He stands by many of the things he said in the post, but given time to reflect, he says it’s more about where he’s at this point in life than the Golden State. “I think it’s the invisibility that I’m chasing, not so much a disdain for California,” he says.

Rich’s California love is motivated by his ties to the people, from family members to world renowned artists.

He says he’s appreciative that his friend, the late Tupac Shakur, has a street named in his honor and that there’s been an arrest in connection to his murder. But Rich would prefer to see Pac alive now, enjoying all he accomplished.

Rich and Pac met around ’91 through a common friend, and became homies; not making music, just hanging out. As Rich’s career was in full swing and Shakur’s was just getting off the ground, Pac asked to be on a track with Rich. “Na, we’re doing gangsta music,” the rapper from the Rolling Hundreds told the young MC from Marin. “You on that Black Power shit.”

The two stayed in contact, though, and Rich watched Tupac’s career explode. When Pac was incarcerated, they exchanged letters; mail that Rich wishes he would’ve kept. With a custom Harley motorcycle parked behind him, painted with Tupac’s face on it, Rich says, “When it’s your homeboy, you not planning on him dying and being one of the most famous people in the world.”

Before his death, Rich saw visible changes in Tupac. “He was moving too fast,” says Rich, who urged him to lead a more private life. But that didn’t happen. Rich had to accept that “my little homie became my big homie,” as he says. So Rich did his best to look out for him in life, and continues to represent for him after his death.

In addition to the customized motorcycle — named Makaveli — Rich has photos, a framed plaque of albums commemorating the songs they recorded together, and a set of coat hangers in the form of middle fingers. (Tupac loved flipping people off.) Rich also has a handwritten contract ensuring songwriting royalties for his contribution to the song “Heavy in the Game,” framed and mounted on the wall in his house — signed by Tupac and his late mother, Afeni Shakur, just months before Tupac’s death.

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ll of the art in Rich’s house is properly positioned. His crib is well-kept and organized. His cars are pristine and his head is shaved clean. It’s all a reflection of who he is, and an extension of the discipline his mother instilled in him.

But there are still times when everything isn’t all put together. Instances when the unpredictable happens, like when he hits the stage and literally breaks a leg. That’s when the cool, calm, collected Rich takes a backseat, and Double R comes out.

“I know what happened that day,” says Rich, reflecting on the day he fell at the Pergola. He suspects that someone else showed up inside of him — someone he’s known for a while.

“He always shows up when I’m in distress,” says Rich. The persona never stays there long enough to introduce himself, but Rich brags, “He’s raw. He knows how to rap, how to ride motorcycles, he knows how to drive cars. Yeah, he’s good at a lot of things.”

The song that started all of this, “What We Doin!?,” was released in June 2024 — with some subtly prophetic lines. On the first verse, recorded weeks before Rich injured his leg while performing the song, LaRussell says “Broke a leg, re-learned how to stand.” In the third verse, Rich advises: “If you know me, never underestimate the OG.” Doctors told him it would take eight months to heal. Four months later he was back on stage.

At The New Parish on that Sunday afternoon in Oakland, Rich was sharp throughout the hour-long performance. A few weeks before the show, LaRussell had pulled some of his favorite Richie Rich tracks and asked if he could add them to the setlist. And though they didn’t rehearse beforehand, the two didn’t miss a beat, going through hit after hit, like Rich’s 2000 track “Playboy” and LaRussell’s 2021 song “GT Coupe.” They reimagined songs in never-before-heard iterations, spanning generations.

The following day, Rich tells me his leg is doing fine. Talking just after getting off the phone with LaRussell, he adds that the younger rapper discussed future collaborations and offered continued encouragement to the rapper who, nearly 30 years after his Def Jam debut, has more than earned the title Seasoned Veteran.

“I didn’t know you was a dog like that, Double,” LaRussell told him. “A unc, you still got it.”