While in prison, Wallace began to take rapping more seriously and wrote the entirety of his debut mixtape while incarcerated. After being released from prison, where he took the name Tee Grizzley, he released his debut single "First Day Out" in November 2016. The music video, posted to YouTube, gained over 2 million views in less than three weeks. He later signed to 300 Entertainment & Atlantic Records in 2017. He released his second single, "Second Day Out", in February 2017. His third single "From the D to the A" featuring Lil Yachty was released in March 2017. He released "No Effort" and its accompanying music video on March 31, 2017. His debut mixtape My Moment was released on April 7, 2017. Grizzley said that his record sales tripled after his song was featured in a LeBron James Instagram post. Grizzley's song "Teetroit" was released on July 28, 2017. The single "Beef", featuring Meek Mill, was released on September 1, 2017. He received two 2017 BET Hip Hop Award nominations for Best New Hip-Hop Artist and Best Mixtape for My Moment. He released the song "Win" on October 6, 2017. He released the song "What Yo City Like" with rapper Lil Durk on November 30, 2017 as the lead single for Bloodas. The two then released the joint mixtape Bloodas on December 8, 2017. He released the single "Colors" on February 2, 2018. The single "Don't Even Trip" featuring Moneybagg Yo was released on March 14, 2018. On March 9, 2018, Grizzley had a feature in Lil Yachty's new album Lil Boat 2 in the song "Get Money Bros.". His debut studio album, Activated, was released on May 11, 2018. In August, he received a 2018 MTV Video Music Award nomination for Push Artist of the Year. He released the mixtape Still My Moment on November 9, 2018. In May 2019, he released the single "Locked Up". On August 20, 2019, his vehicle was shot at in Detroit, Michigan. His aunt/manager Jobina Brown was killed in the shooting, she was 41. He and the driver survived the incident unharmed. On September 20, 2019, Grizzley released his single "Satish" accompanied with a music video to commemorate Brown's death. In January 2020, he released the single "Red Light". In March, he released the single "Payroll" featuring Payroll Giovanni. His song "No Talkin" was featured in the Netflix film Coffee & Kareem. He released the song "I Spy" on May 1.