Fabolous has thrived across decades of New York hip-hop tumult and era turnover by the strength of his unwavering formula: artful punchlines, timely references, flashy hooks, and a calm confidence indicative of his Brooklyn origins. Born John David Jackson (1977), Fabolous got his start the old-fashioned way. He converted street freestyle prowess into radio cameos, and a stunning turn on DJ Clue’s late-’90s Hot 97 show into a deal with the powerhouse host’s Desert Storm label. Fab’s sharp mixtape verses helped the imprint get major label distribution in time for his 2001 debut, Ghetto Fabolous, which showed off an arsenal of slick, street-smart wordplay alongside the type of sing-along romantic cuts that often elude rappers known for raw bars. It was a toolkit that would lead to an unconventionally long, prolific career. He’s stayed in the charts with his own songs like the seductive, P. Diddy-featuring “Trade It All, Pt. 2,” retail therapy anthem “Throw It In the Bag,” and lyrical assault “Breathe,” while also becoming an R&B staple by lending warm nonchalance to songs by the likes of The-Dream and Trey Songz. Despite his platinum plaques for more accessible tunes, Fab never strays far from the ultra-lyrical rap that got him his start, feeding hardcore heads with radio freestyles, the Soul Tape and Summer Shootout mixtape series, and 2017’s Friday on Elm Street joint LP with fellow NYC heavyweight Jadakiss. He’s also been a presence on social media with his fly, occasionally outlandish outfits and witty replies earning nearly as much repute as his raps. No matter the year or climate, Fabolous is always in the mix—and that’s how he likes it.