He first gained recognition in August 2015 for his viral hit "One Night", the lead single from his debut extended play (EP), Summer Songs.

[5] His collaborative album with English singer James Blake, Bad Cameo (2024), further experimented with the genre and was met with continued praise despite failing to chart.

[1] In February 2016, Yachty debuted as a model in Kanye West's Yeezy Season 3 fashion line at Madison Square Garden.

[14] In April 2016, Yachty collaborated with DRAM on the hit song "Broccoli", which peaked at number 5 on the Billboard Hot 100.

[4][15] Yachty released his second mixtape Summer Songs 2 in July 2016 with features from G Herbo, Offset, and his former collective the "Sailing Team".

As part of this appearance, Yachty performed a 'freshman cypher' alongside Denzel Curry, Lil Uzi Vert, 21 Savage, and Kodak Black.

[24][25] The third promotional single, "X Men", produced by 30 Roc and Tillie and featuring a guest appearance from American rapper Evander Griiim, was released on May 18, 2017.

[33] Despite receiving mixed reviews from critics, Lil Boat 2 performed well commercially, debuting at number two on the US Billboard 200, with 64,000 album-equivalent units.

[37][38] The release was accompanied by a 9-minute music video directed by Director X, in which Yachty dresses up as a parody of Oprah Winfrey.

[46] In early 2021, Yachty was reported to be producing and starring in a live-action movie based on the UNO card game, which is being developed by Mattel Films.

[50] Yachty's label and collective Concrete Boys, which includes Karrahbooo, Dc2trill, and Draft Day, released their debut single, "Mo Jams", in December 2023.

[11] Other themes in his works include clouds, cotton candy, the Super Nintendo, and scenes from Pixar films.

[2] Rolling Stone described his music as "catchy, intentionally dinky-sounding tunes packed with off-color boasts delivered in a proudly amateurish singsong.

On February 18, 2022, in a class-action lawsuit filed against the cryptocurrency company SafeMoon that alleged the company is a pump-and-dump scheme, McCollum was named as a defendant along with professional boxer Jake Paul, musician Nick Carter, rapper Soulja Boy, and social media personality Ben Phillips for promoting the SafeMoon token on their social media accounts with misleading information.

[56][57] On the same day, the U.S. 11th Circuit Court of Appeals ruled in a lawsuit against Bitconnect that the Securities Act of 1933 extends to targeted solicitation using social media.

[58] In March 2023, Yachty was among eight celebrities charged by the United States Securities and Exchange Commission, with violating investor protection laws by promoting cryptocurrencies without disclosing that he was a paid sponsor.

The lawsuit was connected with crypto asset entrepreneur Justin Sun's Tronix (TRX) and BitTorrent (BBT) companies.