G Herbo is back on the gas. The Chicago native just released the official music video for “Win Again,” the latest visual from his critically acclaimed project Lil Herb, and it’s everything fans hoped for when he announced a return to the moniker that first put him on the map.

Watch the “Win Again” video here: https://www.youtube.com/results?search_query=G+Herbo+Win+Again

Directed by Mark Cukier of MilkyMadeIt, the video mirrors the tension at the heart of the song itself: the push and pull between elevation and reality. Herbo glides through a fast-paced, unfiltered lifestyle — flying private with his son, touching down city to city, walking straight into studio sessions, and closing out late nights in the club before hitting the road again. It doesn’t glamorize the wins without showing their weight. The grind, the pressure, and the responsibility all sit right on the surface.

What gives the visual its emotional anchor is Herbo’s son, Yosohn Santana Wright, better known as Baby Crash, who cuts through the chaos and reminds viewers that every move, risk, and W carries a deeper purpose. Baby Crash is already making his own mark too, most recently on “Hit The Road” alongside his dad and cousin NoHookChe.

“Win Again” is a standout from Lil Herb, the 15-track homecoming and sonic memoir Herbo dropped back in November. The project has been a career-defining moment, led by the explosive “Went Legit” — recently named the #3 Song of the Year by COMPLEX, RIAA Gold certified, and Herbo’s first-ever Top 10 record on a Billboard radio chart, peaking at #1 on Urban Radio. The album itself debuted at #2 on Apple Music’s all-genre chart and #15 on the Billboard 200.

Early singles “Reason,” produced by Don Cannon, and “Whatever U Want” featuring Jeremih, set the tone — balancing intensity with reflection. That same balance runs through the full tracklist, grounded in work from trusted collaborators like Southside, Chase Davis, OzOnTheTrack, and C-Sick. Features from Anderson .Paak on “Thank Me” and Wyclef Jean on “Emergency” add another layer of depth, bridging perspectives and generations in a way only a rapper this deep in his catalog could pull off.

An extended version of the project followed shortly after release, adding “This N That,” “Hold My Hand God,” and “No Bap,” expanding the autobiographical arc and hinting that the story is far from finished.

“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,” Herbo said of the project. Named after the moniker he broke through with 15 years ago, Lil Herb is 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 to date with “Went Legit” off 2024’s Greatest Rapper Alive, Herbo is now reaching back and looking forward at the same time.

He recorded 100 songs over the course of a year, revisited old favorites, and returned to Chicago studios with his day-ones to land on the final 15. The result blends soulful hip hop, menacing drill, and a handful of guest features that elevate the project’s full-circle feel.

“I’m at the finish line,” Herbo says. “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.”

If “Win Again” is any indication, the Lil Herb era still has plenty of road left. Stream Lil Herb everywhere now, and keep an eye on G Herbo — because the story is still unfolding.