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Fly Anakin
Raised on a steady diet of Ready To Die and Supreme Clientele, equipped with a penchant for dizzying internal rhyme, and damn near impossible to outrap, 27-year-old Richmond, VA artist Fly Anakin has established himself as one of the country’s most essential rappers dedicated to transmuting the rugged spirit of ‘90s New York and sending it spinning into the future. He is linchpin of Richmond’s rap community and the co-founder of the Richmond-based rap collective Mutant Academy. Since 2015, he has released over 25 projects, including many with his inner circle of rap friends, including Tuamie, Ohbliv, Big Kahuna OG, Koncept Jack$on, Henny L.O., and Birmingham hero Pink Siifu. In this span, Anakin has placed collaboration at the core of his artistic identity, and he’s honed his sharp, observational, and sometimes surreal manner and the bulletproof sneer with which he delivers it. All the while, he’s maintained a DIY ethos, recording an estimated 95% of his music at home. His wizardry has garnered extensive praise from Pitchfork, which wrote, “Fly Anakin is a marvel to behold, the kind of lightning-in-a-bottle technician who makes you drop what you’re doing to better absorb his enunciation, syllable placement, and superhuman breath control.” Fly Anakin has been rapping for nearly two decades and it shows—but his prime has only just begun.

Songs

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1
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Creme's Interlude (feat. Creme) E
Pink Siifu
2
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My N*gga E
Fly Anakin, Quelle Chris, $ilkMoney, Big Kahuna Og, and Shungu
3
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Tha Divide (feat. Zelooperz, MAVI & Koncept Jack$on) E
Pink Siifu
4
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Delay The Issue (feat. Fly Anakin) E
Evidence
5
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The Times E
Fly Anakin

Albums

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Forever Dream

2025
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Frank

2022
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The 8's (2014-2018)

2020
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&Friends2

2024
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Pixote

2021
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360 SANTANA

2020
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Skinemaxxx (Side B)

2023
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$mokebreak

2021
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Skinemaxxx (Side A)

2023
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FlySiifu's

2020

Singles & EPs

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New Jersey Drive

Single • 2025
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Suppression

Single • 2023
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mirrors_episode.2

EP • 2022
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Talk To The Mass (feat. Goya Gumbani & Fatima)

Single • 2025
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Stop Tryna Hack My Facebook

EP • 2023
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Black Be The Source

EP • 2022
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YOUGOTME!!

Single • 2024
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Outsidigan's Anthem

Single • 2023
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Intrepid

Single • 2023
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Blicky Bop

Single • 2023

Videos

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Fly Anakin - Affirmations Feat. Pink Siifu (Official Video)

Fly Anakin • 157K views
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Things Change

Fly Anakin, Demae, & Foisey. • 244K views
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Chess Pieces

Foisey & Fly Anakin • 14K views
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Intrepid (Official Video)

Fly Anakin • 148K views
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No Dough (Prod. by Madlib) (Official Video)

Fly Anakin • 217K views

Featured on

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Left-Field Hip Hop

Playlist • YouTube Music

Playlists by Fly Anakin

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Skinemaxxx

Playlist • Fly Anakin • 1.6K views
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“Frank”

Playlist • Fly Anakin • 943 views

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