G Herbo unveils the official video for “Win Again,” a triumphant standout from his critically acclaimed project Lil Herb (November 7). The record finds Herbo balancing hard-earned success while staying true to his code as he navigates loss, loyalty, and the pressure to keep going. “Win Again” captures that cycle in real time, coming off a win and chasing the next while reckoning with its cost.
Directed by Mark Cukier/MilkyMadeIt, the visual mirrors the push and pull between elevation and reality. Herbo moves through a fast-paced, unfiltered lifestyle, flying private with his son, touching down city to city, stepping straight into studio sessions, and living out late nights in the club before heading back on the road. The video doesn’t glamorize the wins without showing their weight. It captures the grind, pressure, and responsibility all at once. His son’s presence cuts through it all, grounding the chaos and reinforcing that each move, risk, and win carries deeper purpose, as Yosohn Santana Wright, also known as Baby Crash, starts making his own mark with a recent release, “Hit The Road,” alongside his Dad and cousin, NoHookChe.
ABOUT G HERBO:
“It’s like finding your roots, getting in touch with your old self and that hunger you had when you first started, the energy that made the world fall in love with Lil Herb,” says G Herbo of his new project, Lil Herb. Named after the moniker he broke through with 15 years ago, it’s both an album and a time machine. After helping invent and globalize Chicago drill, launching the Swervin Through Stress nonprofit, and scoring his biggest hit, “Went Legit” off his 2024 mixtape Greatest Rapper Alive (13M direct-to-fan streams), Herbo is now reaching back and looking forward. He recorded 100 songs over a year, revisited old favorites, and returned to Chicago studios with his day-ones. The result blends soulful hip hop, menacing drill, and a handful of exciting guest features that elevate the project’s full-circle feel. “I’m at the finish line… I’m in full control of my destiny now. I’ve finished the marathon I started when I was 16, when I was Lil Herb.”
