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Fiasco began his career in the early 2000s, where he was part of hip hop crew the 1500s, and distributed street mixtapes. One day, a few record producers invited him to showcase at Raw Dope Studios, where Aftermath Records would be scouting. There, he met his future business partner and manager, Chilly, and became a member of the rap group Da Pak. After the group's disbandment, he briefly signed as a solo artist with Arista Records until CEO L.A. Reid's departure in 2004, leading to many artists being dropped or moved onto subsidiary labels. He then signed a recording contract with Atlantic Records. He gained mainstream recognition with his feature on Kanye West's 2006 song, "Touch the Sky," and achieved solo success with his debut single, "Kick, Push," which became a celebrated anthem for Black skateboarders.

His first studio album, Lupe Fiasco's Food & Liquor (2006), generated critical acclaim for its cerebral and socially conscious lyricism. It was followed by Lupe Fiasco's The Cool (2007), an album exploring themes of street violence, loss, and the allure of all things "cool." Despite encountering label difficulties with Atlantic, his third album Lasers (2011) finally dropped after a fan petition and a protest, becoming his first number one album on the US Billboard 200. His next album, Food & Liquor II: The Great American Rap Album Pt. 1 (2012), delved into the country's sociopolitical issues such as colonialism and racism. Tetsuo & Youth (2015) marked a comeback for Fiasco, receiving widespread acclaim. Drogas Light (2017), his first project off of Atlantic, was critiqued for its sound, in likeness to Lasers, while Drogas Wave (2018) returned to high-concept storytelling, focusing on a group of slaves who survive by living underwater. His latest releases include Drill Music in Zion (2022), described as his Illmatic, otherwise known as his magnum opus, and Samurai (2024), named to be his most personal album yet, inspired by an Amy Winehouse quote.

Through his music, you may learn about child soldiers, the Audubon Ballroom, settler colonialism, Black civil rights leader and activist Dick Gregory, names of slave ships, names of Black lives to be remembered, and conspicuous consumption. You may also, after several listens, catch his use of analogies, wordplay, double entendres, or many pop cultural references.

• He has practiced martial arts since he was three years old. He dedicated his 2019 TV docuseries, Beat n Path, to his late father Gregory Jaco, who was a martial arts instructor, a former member of the Black Panther Party, and an Army Green Beret.
• He considers himself to be a student of Jay-Z, whom he has studied lyrically and respects. In 2010, Jay-Z stated to Cornel West, "I thought [Lupe] was an extraordinary writer […] If you sit down and really listen to some of the things that this young man has said, it's like you can't believe it."
• Along with being a rapper, entrepreneur, lecturer at MIT, and painter, Fiasco has published stories. His short story "This City Is a Robot" was written for the Chicago Sun-Times. "Reflections of a Window Washer" appeared in the print edition of BLAG magazine. He is currently in the process of writing Wave, the accompanying graphic novel to his seventh studio album.
• His final album would've been called LupEND, intended to fulfill his contract with Atlantic Records. However, his label refused to greenlight the project. He confirmed in January 2022 that it was "100% canceled."
• He participated in Nike's 2009 Basketball MVP comedy commercials, voicing the reindeer, Blitzen, who sings a diss track aimed at Santa Claus (voiced by KRS-One).
• He is part of the educational guild Society of Spoken Art, for rappers looking to expand their art through academic studies in language sciences, computation, and cognitive science. Their motto is Firmitas, Utilitas, Venustas (Solid, Useful, Beautiful). He presented the institution at the 2019 Para Site International Conference in Hong Kong, China.
• He wrote an open letter on white supremacy in 2015, where he denounced it and concluded, like everyone else, is "regularity."
• Along with his love of video games, Japanese culture, jazz music, and game of ur, he is passionate about cars.
• He made a cameo on the American drama television series, One Tree Hill (S4, E4), where he performed his songs "Kick, Push" and "I Gotcha" live. Another cameo was on the American musical drama television series, Empire (S4, E12), where he purchases an apartment.
• In collaboration with Google, they created the artificial intelligence (AI) tool, TextFX, to assist rappers, writers, and wordsmiths. It launched to the public on August 2, 2023, where Fiasco created the song "Glass of Water" as an example.