Ryan Leslie seemed determined to document every second of his life in 2008. It was the era of a trillion rap blogs, and R&B’s Truman Burbank was shrewd enough to recognize a voyeuristic platform like YouTube as the next star-making frontier. Whether there was anything that interesting about him as an on-screen personality was beside the point: He wanted music fans to see the nuts and bolts of how a multi-talented singer, songwriter, and producer makes hits, so he recorded himself daily on a Canon GL2 and edited endless hours of footage into webisodes for his YouTube channel, Ryan Leslie TV.
He noticed the clips that got the biggest reactions were his dramatic beat-making sessions, where he bounced like Tigger around a recording studio. In the most talked-about video, with 5.6 million views to date, Leslie wears shades and zips from one instrument to the next, drums to keyboard to Mac, layering the beat for his slinky single “Addiction” until it sounds like a beeper having an identity crisis. The scene is lighthearted, but in Leslie’s eyes, it carries a certain gravitas. “You’re watching and viewing the moment of creation,” he said in a 2019 interview. It’s “the closest we can get to God.”
By the time his self-titled debut album dropped in February 2009, Leslie had meticulously digitized two-plus years of his life on three one-terabyte hard drives. Hip-hop was becoming extremely online, allowing upstarts like him to broadcast their personal lives and creative process in a new way. The nature of celebrity was about to change forever.
Meanwhile, mid-aughts R&B was in a critical transitional stage, with rougher-edged singers like Trey Songz and Jeremih seizing control from smooth-talking traditionalists like Ne-Yo and John Legend. But despite his best efforts to come across as a playboy in his music, Leslie’s artistic persona always fell somewhere between sweet and pretentious. In a world of over-the-top vocalists in constant heat, the former Harvard a cappella singer brought giddy band-virgin energy. So while R&B’s most flamboyant artist-producer, The-Dream, had established himself as a smash hitmaker with a gift for being spiritually crass, Leslie positioned himself as a digital-minded hybrid mogul: a singing, rapping producer with ambitions to be the next Diddy or Tommy Mottola. His ingenuity lay more in his musicianship and marketing than any semblance of edge.
Harmonizing rappers were suddenly everywhere, but Leslie’s entirely self-produced debut coincided with one in particular, arriving three days before Drake’s soft-era-launching So Far Gone—a mixtape inspired partly by the Toronto rap star’s revelation about how brazenly he and his friends spoke about women in private. Leslie’s boastful talk-rap style was inoffensive by comparison. His lead single and album opener, “Diamond Girl,” a blustery club track, casts him as a casanova searching for a leading lady to help him settle down. It’s a splashy introduction for Leslie, presenting him as a capable rapper and one-person band. But when Kanye West and G-Unit each dropped unofficial remixes, it highlighted the difference between their effortless cockiness and Leslie’s more bookish bravado.
Better than some peers, though, Leslie grasped R&B’s conventional ideals of pleading emotion and sincere desire for companionship. Over 12 tracks, he’s drawn to women with an intoxicating presence, excited about how that infatuation might either grow or rip his heart to pieces. On “You’re Fly,” a carefree, flute-driven serenade about graduating to friends with benefits, he’s optimistic, while the jumpy, mid-tempo “Quicksand” and the warm lullaby “Valentine” anticipate new love. The latter and its sister track, “Just Right,” are the closest to ballads on a mostly buoyant album that’s enticing even if it’s notably impersonal. Though eager to share his creative process in his videos, Leslie wasn’t interested in being that transparent about his feelings.
Instead, he leaned into his music-geek impulses and succeeded in creating a signature sound. His production has a breeziness, marked by synth tones programmed to feel like callbacks to the innocent days of pagers and dial-up. You hear it on records like New Edition’s 2004 single “Hot 2Nite” (a beat Leslie originally made for himself) and Cheri Dennis’ 2007 gem “I Love You,” relics of R&B’s evolution to clubby electronic rhythms. While the spaciness of predecessors like Timbaland and the Neptunes inform Leslie’s production style, he has a knack for calibrating his own earworms to sound like Jetsons gadgets coming to life. His trademark glitzy R&B, just downstream of pop radio hitmakers, is charmingly frivolous in a way that Leslie himself isn’t. He told the Washington Post in 2009, “Show me another artist that, without any engineers, without any famous friends, without any famous instrumentalists, without any famous songwriter, without any famous rapper, is just gonna lock himself in the studio with nothing else but a bunch of equipment, walk in there with thin air and within a couple of hours have something that ignites him to the point that it’s visibly infectious.”
Leslie had the confidence of an Ivy Leaguer who’d been called a prodigy most of his life. Born in Washington, D.C., to parents who were both Salvation Army officers and moonlighting musicians, he learned to play piano by ear. Once, when Leslie was about four, he encountered a soda vending machine. “He put his ear against the box and he listened very intently,” his father later told The Harvard Crimson, “and then he started to snap his fingers and bop his head to the rhythm of the Coke box.” Leslie entered Harvard at 15 with a perfect SAT score, majoring in politics while singing and touring with the university’s a cappella group, the Krokodiloes. But already it was clear he’d rather be making beats. At one point, he spent 30 hours a week in the studio while gigging around Boston. In that same Crimson profile in 1998—Leslie’s senior year—he told the paper that he aspired to be “the hardest working man in entertainment.”
After college, Leslie moved back in with his parents and convinced his dad to buy him $15,000 worth of recording equipment on credit. He scored one of his first placements, New Edition’s “Hot 2Nite,” while interning with a producer who worked for Diddy. He landed more high-profile gigs after signing to Tommy Mottola’s Universal imprint, Casablanca, in 2003, producing filler cuts for mega-stars like Britney Spears, Beyoncé, and LL Cool J. His own planned first album got shelved, but Leslie had already found the artist who’d help him fulfill his mogul dreams. He met Cassie, then an 18-year-old model, at a nightclub in 2004, and they struck up both a working and personal relationship, which was initially kept under wraps.
As the music industry scrambled to understand social media’s potential, Leslie adapted. He used MySpace as a digital billboard, attracting followers with photos and videos of Cassie—and, eventually, a song. That online popularity helped catapult her bubbly 2006 breakout “Me & U” (which Leslie produced) to No. 3 on the Billboard Hot 100, creating a new blueprint. Artists like Cassie and, later, Soulja Boy (whose 2007 sensation “Crank That” broke on YouTube) proved how quickly an unknown musician could turn internet notoriety into offline fame. “Ryan launched and promoted a completely unknown artist who went to No. 1 for seven weeks as a result of a viral experience. Normally, I would think that would be a mountain too high to climb,” Mottola told The Boston Globe in 2008, citing the U.S. Airplay chart. Leslie, he said, was “very plugged into the new technology that’s going to be a critical piece of how music is made and distributed.”
“I’m at 100,000 friends on MySpace and 14,000 plays a day on my little music player,” Leslie told the Globe in the same article, months before his debut’s release. His digital-first approach signaled where the music business was headed, with social media as a primary metric. “I’d love to be at 60,000 plays and half a million friends,” he continued. “In the meantime I can be making records, continuing to be really strongly entrenched in the online video community, releasing behind-the-scenes stuff. And when there’s an insane, incredible demand for my album that cannot be contained anymore, I can put it out tomorrow.”
Diddy noticed the success of “Me & U,” too. He signed Cassie to Bad Boy, calling Leslie the “new-age Teddy Riley.” It was the partnership that nourished a thousand gossip blogs, fueled by rumors that Cassie had dropped Leslie as both a producer and boyfriend and entered a relationship with Diddy. Unlike Usher, who’d drawn on his own messy celebrity dating life for 2004’s career-making Confessions, Leslie didn’t attempt to capitalize on the ensuing love triangle in his music. But he has said his split with Cassie quietly inspired records like “Diamond Girl” and “Out of the Blue,” where he reflexively blames both parties for a breakup over a spiraling ringtone of a beat. “I should’ve been a better friend,” Leslie suggests, then wonders, “What would you do?/If I left you out of the blue?/Would you fight back tears while your heart gets torn to pieces?”
The upbeat mid-album track “How It Was Supposed to Be” explores a similarly tense feeling of abandonment, and on the pulsing “Shouldn’t Have to Wait,” Leslie is guilty of making a woman wait on him to settle down. Then he recovers optimism on odes like “Wanna Be Good” and the fanciful “Irina,” where he falls victim to love at first sight. Alluringly shallow, the album is zippy and playful, an effusive pitch from an artist whose plainest objective as a singer and sometime rapper is to go get the girl.
In June 2009, four months after the release of Ryan Leslie, PC Mag reported that Facebook had surpassed MySpace in popularity for the first time. Twitter and Instagram soon emerged as the next permanent fixtures for artists looking to build a fanbase. Leslie, naturally, maintains a presence on all of them. Coming up in the cosmic stew of social media and streaming has allowed Leslie to, years later, maintain a following and embark on a career as an entrepreneurial spokesperson. In the influencer era, an internet-savvy self-starter no longer needed Diddy-level music fame to operate like a mogul.
The same year as his debut, Leslie released a subtly thrilling follow-up, Transition, inspired by a summer rendezvous, and later recorded a full-on rap album, 2012’s Les Is More. Clips of his old studio sessions still circulate on social media, passed along by a faithful subset of fans like treasure maps leading to a lost gem of an album. Posted in June 2008, a low-resolution video for the making of closing track “Gibberish” shows him taking what looks like a piccolo trumpet out of its case. The song’s concept is ridiculous—Leslie mumbling sweet nothings to convey speechlessness. But it’s also oddly the album’s most sensual moment and one of R&B’s most inventive uses of Auto-Tune’s warbling effects. In the video, Leslie plays his trumpet into the mic in a recording booth and later procedurally returns it to its case. As much as he loved creating, he also seemed to enjoy performing the part of being an artist—no matter how extra it sometimes appeared on camera. Any musician with an online presence now does the same; behind-the-scenes content is de rigueur. But there’s still something endearing about a beatmaker with an ego and a bunch of instruments who cared about showing the work.