Bennett was born on August 9, 1994, in Chicago, Illinois.^[10] He had six half-siblings from his father, Walter E. Bennett, and three siblings from his mother, Taesha. He was raised mostly by his mother in the Parkway Garden Homes in South Side, Chicago's Greater Grand Crossingcommunity area, more commonly known as "O-Block".^[1][11] His relationship with his father was inconsistent due to his father's incarcerations. When Von was 11 years old, his father was killed by an unseen gunman. Von later paid tribute to his father in multiple songs.^[12]

King Von was present for the birth of drill music through his association with Chief Keef and Lil Durk. However, he was frequently incarcerated throughout the 2010s for a multitude of serious criminal charges, which made him known in Chicago's drill scene even before he began recording music.^[13]

At age 16, Bennett went to juvenile detention for armed robbery in January 2011. While incarcerated, Bennett earned his GED. After being released, Bennett attended a few classes at South Suburban College in South Holland, Illinois, before dropping out.^{[14][better source needed]}

In July 2014, Bennett was charged with one count of first-degree murder and two counts of attempted murder in connection with a shooting that killed one and injured two others.^[15] After being detained in Cook County jail for over three years, he was acquitted in December 2017 and began his musical career.^[16]

Upon Von's release from jail in December 2017, fellow rapper Lil Durk signed Von to Durk's Only the Family label. Von then released a series of singles. The first of these singles was "Beat Dat Body", which featured fellow Chicago rapper THF Zoo, and was released on June 17, 2018.^[17] Von subsequently appeared on the Lil Durk Presents: Only The Family Involved album, which was released on July 31, 2018. He featured on the song "Problems", which had an accompanying music video released on August 9, 2018.^[18] Von then released the single "War With Us" on October 18, 2018.^[19] Von's single "Crazy Story" was released on December 6, 2018.^[20] It became his breakout single, reaching number 81 on Billboard Hot 100.^[21][22]

On January 9, 2019, Von was featured on the remix of "Exposing Me", a song by fellow Chicago rapper Memo600. Von and Memo600 swapped bars disrespecting and detailing real life feuds and altercations against other nearby neighborhood rivals. A response from the targets arose when rappers FBG Duck and Rooga dropped their own remix of the song on February 4, 2019. Both songs were produced off the sampling of original Indian song Sanam Re. Following the success, a series of remixes for the song were made by other artists both in the United States and in Europe^[23][24]

On February 14, 2019, Von's then-girlfriend, rapper Asian Doll, released a music video for her track about him, "Grandson", in which he appeared.^[25]

In May 2019, "Crazy Story 2.0" featuring Lil Durk was released, and a music video was later released on May 20, 2019; the song peaked at number four on the Bubbling Under Hot 100 chart.^[26][27] On September 13, 2019, a third rendition of the single called "Crazy Story, Pt. 3" was released.^[28] On July 9, 2019, Lil Durk and King Von released their collaborative single "Like That".^[29]

On September 2, 2019, Von released his single "What It's Like", as the single forerunner of his first mixtape album announced in September 2019.^[30]

The mixtape was dropped some weeks later on September 19, 2019, it consists in 13 a tracks mixtape, and it is named Grandson, Vol. 1, executively produced by Chopsquad DJ, it contains three features represented by "Twin Nem" and by the Remix of "Crazy Story" both featuring Chicago artist Lil Durk; the other feature consists on the collaboration with Chicago artist and OTF affiliate Booka600 on "Jet". The mixtape also includes tracks "Crazy Story", "Crazy Story, Pt. 3", and his second ever single "War With Us" dating back to October 18, 2018.

Grandson, Vol. 1 debuted at number 75 and later peaking at number 53, on the Billboard 200, also it reached number 27 on the Hip Hop/R&B albums chart, and number 9 on the Independent album chart.^{[31][32][33][34]}