Following his rise to fame, record producer Rico Beats introduced Pop Smoke to Steven Victor in April 2019.

His second mixtape, Meet the Woo 2, was released on February 7, 2020, and debuted at number seven on the Billboard 200, becoming the rapper's first top-10 project in the United States.

In late 2018, he was rapping over a beat from 808Melo's YouTube channel, Jackson recorded a track titled "MPR (Panic Part 3 Remix)" during the session.

[11] From October to December 2019, Jackson released multiple singles, including "War" with Lil Tjay,[12] and "100k on a Coupe" with Calboy.

[13] On December 27, 2019, Jackson appeared on Travis Scott's Cactus Jack Records compilation album JackBoys on the song "Gatti" which was also accompanied by a music video.

[17] On February 7, 2020, twelve days before his death, Jackson released his second mixtape Meet the Woo 2, with features from Quavo, A Boogie wit da Hoodie, Fivio Foreign and Lil Tjay.

[15][23][24] At the beginning of March 2020, American rapper 50 Cent announced on his Instagram that he had decided to executive produce and finish Jackson's debut studio album.

[25][26] After his announcement, 50 Cent called artists like Roddy Ricch, Drake, and Chris Brown, wanting to feature them on the record.

[36] All 19 songs on the album charted on the Billboard Hot 100,[23] with "For the Night" featuring Lil Baby and DaBaby, debuting and peaking at number six, giving Pop Smoke his first top-10 hit in the US.

[38] The album's fifth single "What You Know Bout Love", ended up peaking at number nine on the Billboard Hot 100, giving Pop Smoke his second top-10 hit in the US.

[45] On January 17, 2020, after returning from Paris Fashion Week,[46] Jackson was arrested by federal authorities at John F. Kennedy International Airport after stealing a Rolls-Royce Wraith, valued at $375,000, whose owner reported it stolen after Jackson had reportedly borrowed it in California for a music video shoot on the condition it would be returned the next day.

[47] He was charged with grand theft auto, posted a $250,000 bond, and agreed to stay away from known gang members and submit drug tests to the US pretrial services.

[49] The conditions Jackson was put under hindered some of his performances like the "BK Drip Concert" at Kings Theatre in Flatbush in February 2020, as gang members were in the audience.

[47] Jackson rented a house through Airbnb owned by Teddi Mellencamp and her husband, Edwin Arroyave, in Hollywood Hills, California, where he was murdered on 19 February 2020.