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

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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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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No Dough

Single • 2022
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Intrepid

Single • 2023
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Blicky Bop

Single • 2023
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Suppression

Single • 2023
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mirrors_episode.2

EP • 2022

Videos

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My N*gga

Big Kahuna OG, Shungu, $ilkMoney, Quelle Chris, and Fly Anakin • 152K views
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Outsidigan's Anthem (Official Video)

Fly Anakin • 28K views
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Intrepid (Official Video)

Fly Anakin • 147K views
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Fly Anakin - Affirmations Feat. Pink Siifu (Official Video)

Fly Anakin • 155K views
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No Dough (Prod. by Madlib) (Official Video)

Fly Anakin • 216K 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 • 908 views