Toronto Rappers Who Made It to Hollywood: Drake, Maestro Fresh Wes, Infinite & DAN-E-O

Toronto has long been a breeding ground for hip-hop talent, but some of its most legendary rappers have also made waves in Hollywood. From Drake’s global superstardom to Maestro Fresh Wes’ groundbreaking achievements, Infinite’s raw authenticity, and DAN-E-O’s underground legacy, these artists have expanded their influence beyond music and onto the big screen.

In this deep dive, we explore their journeys—from their early days in Toronto’s rap scene to their transitions into film and television. Through exclusive interviews, behind-the-scenes insights, and rare footage, we’ll uncover how these trailblazers shaped the culture and inspired future generations.

Whether you’re a hip-hop enthusiast, a fan of Toronto’s cultural scene, or just love a great success story, this is your chance to witness the evolution of these iconic artists and their impact on Hollywood.

DRAKE’S ACTING CAREER

Drake’s acting career started long before he became a global rap superstar. Born Aubrey Drake Graham, he gained early fame through television, particularly in Canada, before making a full transition to music.

Breakout Role: Degrassi: The Next Generation (2001-2009)

Drake’s most famous acting role was Jimmy Brooks on Degrassi: The Next Generation. His character was a high school basketball star who became paralyzed after being shot in a school shooting episode. He appeared in over 100 episodes between 2001 and 2009, earning recognition for his emotional performance.

Other Acting Roles & Cameos

After Degrassi, Drake focused on music but made a few appearances in film and TV:

• Charlie Bartlett (2007) – A small role in this comedy-drama starring Anton Yelchin and Robert Downey Jr.
• Saturday Night Live (2014, 2016) – Hosted twice, showcasing his comedic skills through sketches and musical performances.
• Anchorman 2: The Legend Continues (2013) – Had a cameo in the film’s famous street battle scene.
• Ice Age: Continental Drift (2012) – Voiced a character named Ethan, a young mammoth.

Return to Acting?

Drake has hinted at returning to acting, and his production company, DreamCrew, has been involved in TV and film projects, including HBO’s Euphoria. Though music remains his primary focus, he has the industry connections and talent to make a major acting comeback if he chooses.

Would you like a breakdown of his best Degrassi moments?

MAESTRO FRESH WES

Notable Acting Roles

• The Listener (2009-2014) – Maestro had a recurring role as Detective Merryweather in this Canadian supernatural drama series.
• Metropia (2004) – He played Quincy, appearing alongside well-known Canadian actors in this urban drama.
• Paid in Full (2002) – He had a small role in this cult classic crime drama, produced by Roc-A-Fella Films.
• Four Brothers (2005) – Starring Mark Wahlberg and André 3000, this crime thriller featured Maestro in a supporting role.
• Instant Star (2005-2008) – A popular Canadian TV series where he had a recurring role as Darius Mills, a tough music industry executive.
• How She Move (2007) – A Canadian dance film where he played a mentor figure in the underground dance and music scene.

Other TV Appearances

In addition to acting, Maestro has made guest appearances on shows like Republic of Doyle, Mr. D, and The Line. He’s also been involved in voice acting and hosting, showing his versatility in entertainment.

Legacy in Acting

Though he remains a hip-hop icon, Maestro Fresh Wes has successfully balanced his music career with acting, proving his talent extends beyond rap. His presence in both Canadian and Hollywood productions has helped pave the way for future artists looking to transition into film and television.

DAN-E-O ACTING CAREER

DAN-E-O, born Daniel Faraldo, is best known as a pioneering figure in Canadian hip-hop, but he has also built a notable career in acting. His work in film and television showcases his versatility beyond music. Daniel Faraldo is known for Lifechanger (2018), Tapped Out (2014) and Breakout Kings (2011).

INFINITE ACTING CAREER

Toronto rapper Infinite, best known for his 1990s hip-hop classics like Gotta Get Mine, has also had an acting career, appearing in several notable film and TV projects. His transition into acting allowed him to showcase his talents beyond music, often taking on gritty and streetwise roles that matched his lyrical style.

In 1999, Infinite was chosen by Capcom to contribute to the soundtrack for the video game Street Fighter III: 3rd Strike, performing voiceovers, as well as three songs. He also held a small acting role in the 2004 biopic Redemption: The Stan Tookie Williams Story.