He has most notably collaborated with Juice Wrld on music videos such as "All Girls Are the Same", "Lucid Dreams", "Robbery", "Bandit" and "Tell Me U Luv Me".

Also, he has directed other music videos such as YG Marley's "Praise Jah in the Moonlight", Lil Yachty's "Poland", Lil Tecca's "Ransom", Internet Money, Gunna, Don Toliver and Nav's "Lemonade", Eminem's "Godzilla", "Gnat" and "Tobey", JID's "Off Deez", Wiz Khalifa's "Fr Fr", YNW Melly's "Mixed Personalities", and many others.

He went to Plano High School and he dropped out of DePaul University to focus on his career in videography and hip hop music, things he had been interested in since childhood.

[2] Bennett originally founded Lyrical Lemonade as an internet blog when he was a high school student in Plano, Illinois.

He began directing music videos for local Chicago rappers, such as Vic Mensa, Taylor Bennett (no relation), King Louie,[3] and Ridgio,[4][5] all of which he uploaded onto the Lyrical Lemonade channel.

[9] He later directed numerous music videos for hit songs, which include Ski Mask the Slump God's "BabyWipe", Lil Skies' "Red Roses" and "Nowadays", and YBN Nahmir's "Bounce Out with That".

In May 2018, he directed the music video for Chicago rapper Juice Wrld's "Lucid Dreams", which peaked at number 2 on the Billboard Hot 100.

[22] Other examples include Pump's friend and frequent collaborator Smokepurpp, Juice Wrld, Ski Mask the Slump God, YNW Melly, Lil Tecca, NLE Choppa, Lil Mosey, The Kid Laroi, Yeat, Trippie Redd, and Jack Harlow.

On the same virtual store front, Bennett occasionally allows fans to purchase props previously used in Lyrical Lemonade videos.