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ST. LOUIS — J-Kwon says he hums Shaboozey’s “A Bar Song (Tipsy)” in his sleep.

The St. Louis rapper is joking, but the breakout single samples J-Kwon's 2004 hit “Tipsy” and has broken records since its release. It's one of Billboard’s longest-running No. 1 hits of 2024, and Shaboozey is the first male artist to top Billboard's Hot 100 and Hot Country Songs charts simultaneously.

The song, off Shaboozey's "Where I've Been, Isn't Where I'm Going" album, unleashed a surge of bar-loving, beer-chugging vibes onto the airwaves. It also sparked nostalgia among those who remember listening to “Tipsy,” J-Kwon's debut single — and a resurgence for J-Kwon himself.

While the song might not be J-Kwon's actual bedtime lullaby, he hummed the country tune as he walked around the exterior of Caldwell Package Liquor Store on North Grand Boulevard in St. Louis for a recent photo shoot.

Twenty years ago, J-Kwon shot the music video for his song "Hood Hop" in this exact spot.

Now, on a mild mid-September day, he's playful, joking with a photographer as he finds the perfect place to stand near a mural of himself on the store's back wall. A serious expression crosses his face as he seeks out a comfortable pose, dusting off his white long-sleeved crew neck and adjusting his hat, both adorned with St. Louis Cardinals logos.

After the photo shoot, J-Kwon digs his all-white Air Force 1 shoes into the ground and claps his hands together, resuming his low, cheerful murmur of the catchy hook from "A Bar Song." He's proud of the song and calls Shaboozey a "hell of an artist."

"It couldn't have been done any better than how it was done," he said. "I thank God for it all."

The rapper is also thrilled about the song's re-emergence in country music for a new generation of listeners. Shaboozey initially contacted him about sampling "Tipsy" with a country twist. Empire president Tina Davis helped the pair structure the deal, resulting in the genre-bending hit. 

J-Kwon said that while "Tipsy" was always a crossover record, he knew it was "unheard of" for a Black male singer to dominate in country music with a song inspired by a hip-hop record.

"You take a Top 40 pop record and redo it with a brother from the streets, that's a no–no," he said. "We had all odds working against us.”

The popularity of "A Bar Song" has provided a comeback of sorts, but J-Kwon wants everyone to know that he never left the scene. 

When he hit the stage with Shaboozey at the BET Awards in June, the crowd screamed as the country star introduced "Mr. Tipsy himself." J-Kwon then launched into his 2004 single, blending it with Shaboozey's new hit. In mid-October, J-Kwon performed "Tipsy" again during rapper Nelly's American Music Awards set alongside Chingy and the St. Lunatics. 

And J-Kwon, who now lives in O'Fallon, Mo., is still finding new ways to evolve creatively.

He made his acting debut this year in the film “Blood Brothers,” which ranked as the No. 3 independent Black film on Tubi. He dabbles in other business ventures, like his clothing brand Expensive Taste. And he runs his record label Hood Hop Music locally, focusing on developing new artists such as pop singer Liyah London and rapper Kane Koca.

While he's often in the studio creating his own music, he says his priority is the success of his artists.  

“I'm just trying to really steer these guys to be bigger and better than me," he said.

Success for J-Kwon came early, when he was barely 18. He roared onto St. Louis' hip-hop scene with his hit song, which stayed on Billboard's Hot 100 chart for 14 weeks and peaked at No. 2. He was a high school drop-out at the time, having spent most of his teen years on the streets after leaving Normandy High School. 

“The ‘Tipsy’ experience was surreal to me because I knew it was over at that point,” J-Kwon said. “I knew all my suffering was coming to a complete halt."

'Something about his charisma' 

J-Kwon, born Jerrell Jones, grew up in the Murphy Blair housing projects in St. Louis with his single mom and older twin brothers. His family moved around a lot, bouncing from south city to Baden, and even briefly living in Illinois. Jerrell and his brothers spent most of their time with their grandparents.

His mother had a heavy work schedule. His father wasn’t around.

His mother pushed him to excel academically, but Jerrell had grown up around drug dealers and crime, so it wasn't a surprise he took the same route.

“I didn't want to take that path," he said, "but I knew it was going to go that way.”

But Jerrell also gravitated toward music. He remembers singing in the bathroom mirror when he was in elementary school, crooning and reenacting music video scenes from R&B artist like Soul For Real and Usher. He’d record beats on an old-school tape recorder and replay it on another to capture his vocals, creating his own childhood studio.

Music, he said, was all he had to live for. He left home at 12, choosing the street life over his mom's rules. Eventually, a family member in south city gave him a place to stay. He also slept in a “deuce and a quarter,” a nickname for a 1959 Buick Electra 225.

Then he met local promoter and music manager Sean “BD” Caldwell.

It was 2001 and Caldwell was making moves as a concert promoter while working with musical acts. His barber mentioned some boys in the neighborhood with raw talent making music. When they arrived to meet Caldwell at the shop, he was surprised to see how young they were.

One of them was Jerrell.

“It was just something about his charisma,” Caldwell said. “He just had this presence about himself that demanded respect.”

After having Jerrell perform, Caldwell asked about the boy's musical aspirations. The young rapper replied that he just wanted a pair of Jordan sneakers.

Caldwell later bought a pair of Jordans and drove to the south side to find Jerrell. That was when Caldwell realized the teen was homeless. Jerrell's story “stole his heart,” he said, and Caldwell became a father figure to him.

He moved Jerrell in with a relative, and the two kicked off a five-year development period, with Caldwell molding the rapper into an artist. Formerly known by the nickname J-Rell, the rapper adopted the stage name J-Kwon in 2000 — paying homage to a scene in the film "Jerry Maguire" where Cuba Gooding Jr.'s character explains that "some dudes might have the coin, but they'll never have the 'quan'... it means love, respect, community and the dollars too."

Caldwell cycled through a few producers, finetuning J-Kwon's sound, before striking gold with “Tipsy.”

“I knew what I had,” he said.

St. Louis was getting buzz in the hip-hop scene in the early 2000s, with Nelly’s “Country Grammar” album and singer Toya's 2001 single “I Do!” climbing the charts. Local production team the Trackboyz made headlines after a Grammy nomination for their work on the Nappy Roots' 2002 song “Po’ Folks.” They also produced the Nelly song “Air Force Ones.”

Caldwell contacted producer and Trackboyz member Mark “Tarboy” Williams to see if he’d be interested in working with J-Kwon. After hearing him rap over the phone, Williams signed J-Kwon to the Trackboyz label. He later connected the dots for the rapper to sign a record deal with Arista and SoSo Def.

J-Kwon lived with Williams while the producer oversaw the “Hood Hop” album creative process. He produced the “Tipsy” beat, partially inspired by the drum pattern from the 2002 Clipse song “Grindin’,” and combined it with some hi-hat rolls to make it more mainstream. It was the last song recorded for “Hood Hop,” which was released in April 2004.

“I always knew that it was in him,” Williams said. “My job, to me and being a producer, is to push the artist to the next level.”

One-hit wonder?

Despite the success of “Tipsy,” “Hood Hop” didn’t reach the same heights as its debut single. The album hit No. 46 on the U.S. Top R&B/Hip Hop Albums chart but didn’t break the top 100 on Billboard.

Critics were unimpressed by “Hood Hop.” All Music’s Andy Kellman described J-Kwon as “an adequate-at-best MC.” In 2019, USA Today included J-Kwon's “Tipsy” in its “One-Hit Wonders of the ’90s and ’00s” Spotify playlist.

Caldwell said "Hood Hop" was intentionally steered toward fun because J-Kwon was a minor when the album was recorded. J-Kwon's bars leaned into his experiences growing up in street and drug culture, so Caldwell and Tarboy helped him create songs that were playful while still shining a light on his real-life experiences.

“We made it a party song, and we made it basically a party album, because we were trying to walk a fine line,” Caldwell said, emphasizing that J-Kwon was “still just a child.” The rapper turned 18 a week before the album was released.

Today, "Tipsy" remains J-Kwon's sole hit record. It has landed on television shows, a video game and films including "White Chicks."

J-Kwon faced legal issues in his early adult years, including fighting a child-support case for a child that he claimed wasn’t his. He was even declared “missing” in 2010 on social media — a rumor the rapper and his label cleared up a month later. 

While he has released three independent albums since his time at the top of the charts, none of them has garnered mainstream success.

J-Kwon, though, doesn't mind.

“People always look at s--t like something is wrong or off,” he said. “No, God's got it set right. You're wrong and you're off if you don't have belief and the faith.”

'A beautiful merger'

Caldwell described “Tipsy” as a gift that won’t stop giving, and he described  “A Bar Song” as a beautiful merger between two artists. The hit song, he said, is J-Kwon's “magic baby,” resurrected at the right time.

“It's a great feeling just to see that work that we did 20 years ago is still paying off right now,” Caldwell said.

Caldwell, owner of the liquor store where the "Hood Hop" video was shot, added the mural to the back wall in 2022. Painted by Tony Holmes, the images depict what Caldwell calls St. Louis' "big four" of hip-hop, with portraits of J-Kwon, Chingy, Huey and Nelly. The mural captures a time when the city rocked the music charts.  

Today, J-Kwon is focused on molding a new generation of musical acts. He uses his experience to teach them about the creative process, persistence and understanding that success doesn't always happen overnight.

Koca, the rapper, signed with J-Kwon's Hood Hop Music label 15 years ago. J-Kwon helped him pick a new stage name — he was previously known as Lou Kane — while teaching him the ins and outs of the music business and critiquing his stage presence.

Koca said he knew "A Bar Song" was a hit from the moment J-Kwon let him hear the record.

"'Tipsy' was so massive itself, and to do it in country and it still be a great song, I knew it would take him all the way over the top," Koca said. "And it's doing exactly that."

For his part, J-Kwon is happy to ride the high from a fresh wave of “Tipsy” love.

"'Tipsy' is forever," he said. "'Hood Hop' is forever."