Chicago’s own Twista receives Legend Award at From The Go Fest
Twista Awarded the Legend Award at From The Go Fest
Chicago’s fastest rapper just earned one of the city’s highest cultural honors. Hip-hop icon Twista received the Legend Award at the From The Go Fest, a youth-led cultural event created to celebrate, empower, and uplift the voices of young Black and Brown Chicagoans. The moment, which took place at Douglass Park on Chicago’s West Side, was met with cheers, emotion, and overwhelming love from fans of all ages.
The award recognized Twista’s decades-long career, contributions to Chicago music, and his continued advocacy for youth development and violence prevention. As the first-ever recipient of the From The Go Fest Legend Award, Twista made history in a city he helped put on the map.
Twista’s Iconic Footprint in Music
Twista, born Carl Terrell Mitchell on November 27, 1973, has solidified his place as one of hip-hop’s most technically skilled and culturally impactful artists. Hailing from Chicago’s West Side, Twista made history in 1992 when Guinness World Records named him the fastest English-speaking rapper in the world, clocking in at an astonishing 598 syllables in 55 seconds. That early recognition set the tone for a career built on speed, lyricism, and longevity.
Twista burst onto the national scene with his 1991 debut album Runnin’ Off at da Mouth under the moniker Tung Twista. Introducing the world to his unique “chopper” style of rapid-fire delivery. While it earned him underground acclaim, it wasn’t until 1997—when he appeared on Do or Die’s Chicago anthem Po Pimp—that Twista truly became a Midwest staple. That collaboration, produced by The Legendary Traxster, opened doors for a major label deal with Big Beat and Atlantic Records. In 1997, he dropped the classic Adrenaline Rush. A project still hailed as one of the most influential Midwest rap albums of all time.
However, it was his 2004 breakthrough album Kamikaze that catapulted him into mainstream stardom. Fueled by the smash single Slow Jamz, produced by fellow Chicago icon Kanye West and featuring Jamie Foxx, the song shot to No. 1 on the Billboard Hot 100. Making Twista a household name. Kamikaze itself debuted at No. 1 on the Billboard 200. A feat that marked a historic moment for a Chicago-born independent rapper.
An Influence Beyond Music
Beyond his musical success, Twista has remained deeply rooted in Chicago’s cultural and social fabric. His career has already cemented himself as a bridge between hip-hop generations. Through his GMG Entertainmentlabel, Twista has consistently mentored young talent and provided platforms for new voices in the city.
Twista’s community involvement extends well beyond music. He’s partnered with schools for youth writing workshops and organized anti-violence initiatives. While also donating professional-grade studio equipment to local community centers on the West Side. Whether he’s speaking at a gun violence prevention panel or appearing at city-led cultural festivals, Twista’s commitment to uplifting underserved communities in Chicago is unwavering.
Given his chart-topping success and heartfelt commitment to his hometown, Twista was the clear and deserving choice for the Legend Award at From The Go Fest 2025. The honor not only celebrated his decorated past—it recognized his ongoing impact on Chicago’s youth, music, and cultural identity.
As fans put it on social media:
“Twista IS Chicago. This award was long overdue.”
“He opened doors for every fast rapper and every kid from the West Side with a dream.”
“The GOAT of speed rap, and one of the realest to do it for the city.”
Twista’s journey—from Guinness World Record holder to Billboard chart-topper to community builder—embodies everything From The Go Fest stands for: perseverance, representation, and pride in Chicago’s youth and culture.
Accepting the award, Twista told the crowd:
“This honor means everything because it’s coming from the youth—from the future of our city. If my music or my story inspired even one of y’all to keep pushing, then I’ve done my job.”
From The Go Fest: A Youth-Led Celebration With Purpose
From The Go Fest 2025 wasn’t just another summer concert—it was a full-blown cultural movement. Designed to honor youth perspectives while showcasing their creativity and leadership, the festival featured live performances by emerging local artists, interactive exhibits, a vendor fair, networking zones, and job and educational resources tailored to Chicago teens and young adults.
The one-day event was spearheaded by True Star. A media company and youth development organization founded by DeAnna McLeary-Sherman and Na-Tae’ Thompson. Their mission? To give underserved youth from the city’s South and West Sides access to real-world media, tech, and business skills that translate into job readiness and economic mobility.
With over 250 paid jobs for youth annually and a powerful digital media platform, True Star is helping young Chicagoans reimagine their futures. From The Go Fest is the latest example of that mission in action.
The True Star Foundation: Empowering Chicago’s Youth Through Media
At the heart of From The Go Fest is the True Star Foundation, founded in 2004 with a vision to empower youth through media education, storytelling, and entrepreneurship. What began as a newsletter program to improve teen writing has evolved into a full-service youth-led media company and digital agency that reaches thousands of students across Chicago.
Since 2007, True Star has trained over 10,000 youth, many of whom come from under-resourced neighborhoods on the South and West Sides. Today, their programs offer hands-on opportunities in digital marketing, journalism, video production, podcasting, graphic design, and more.
But what truly sets True Star apart is that youth aren’t just participating—they’re leading. Young people help run the business, shape content, and work directly with professional mentors.
From the Go Fest Highlights: Music, Vendors & Community
This year’s From The Go Fest 2025 lineup included local talent showcases, breakout music acts, dance crews, DJs, and more. Popular artist like Lil M.U., Sherrionn, Genesis Denise Hale from Showtime’s The Chi and other’s graced the stage. Vendors sold everything from handmade jewelry and candles to custom clothing and zines created by Chicago business owners. Vitaminwater and Sprite Tea were also partners of the event, passing out free samples of both to the crowd.
Attendees could also explore career booths hosted by tech companies, media outlets, colleges, and nonprofit organizations offering job readiness training. The interactive vibe—part music fest, part resource fair—reflected the festival’s mission: to blend culture, creativity, and opportunity.
In the words of co-founder DeAnna McLeary-Sherman:
“We’re not just putting on a show. We’re building a movement that centers youth power.”
Twista’s Legacy and Future in Chicago
Even after decades in the game, Twista remains a respected cultural pillar in both hip-hop and his hometown of Chicago. His contributions span far beyond music—he’s mentored emerging artists, championed gun violence prevention, and supported mental health awareness through his GMG Entertainment label and numerous nonprofit partnerships.
In recent years, Twista has partnered with local schools for writing workshops, hosted community forums on anti-violence, and donated studio equipment to neighborhood centers on the West Side. His presence at From The Go Fest 2025 not only celebrated his legendary status—it underscored his unwavering dedication to empowering Chicago’s youth.
Twista stands alongside other hip-hop giants from Chicago like Kanye West, Common, and Lupe Fiasco, who’ve helped shape the sound and message of hip-hop on a global scale while never forgetting their roots. Together, they form a legacy of lyrical brilliance and hometown pride that continues to inspire new generations of talent emerging from the city.
Fans took to social media to celebrate Twista’s moment, with posts like:
“Twista deserves ALL the flowers. Chicago legend for real.”
“From The Go Fest showing the youth what it means to uplift our own.”
“A full-circle moment. Thank you Twista and True Star!”
A Tribute to Chicago Hip-Hop
The Twista Legend Award 2025 isn’t just a trophy. But rather a symbol of what happens when generations connect to empower each other. For young attendees at From The Go Fest, the honor was a reminder that greatness can come from their streets, their schools, and their stories.
By highlighting a local legend through a youth-led platform, the event bridged past and present, tradition and innovation. It offered inspiration, resources, and community all in one space—something increasingly rare in the festival world. As Twista continues to expand his musical influence, his lasting impression is embraced more everyday.