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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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Tha Divide (feat. Zelooperz, MAVI & Koncept Jack$on) E
Pink Siifu
3
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My N*gga E
Fly Anakin, Quelle Chris, $ilkMoney, Big Kahuna Og, and Shungu
4
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When Thugs Cry E
Fly Anakin, Koncept Jack$on, & Foisey
5
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Mind Right (feat. Liv.e) E
Pink Siifu

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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Socks Over the Smoke Detector (feat. Quelle Chris, $ilkMoney & Fatima)

Single • 2025
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YOUGOTME!! (Clean Edit)

Single • 2024
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Suppression

Single • 2023
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New Jersey Drive

Single • 2025
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YOUGOTME!!

Single • 2024
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Stop Tryna Hack My Facebook

EP • 2023
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Talk To The Mass (feat. Goya Gumbani & Fatima)

Single • 2025
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Intrepid

Single • 2023
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The Times

Single • 2025
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Things Change

Single • 2023

Videos

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FLY ANAKIN - MY N*GGA ft. Quelle Chris, $ilkmoney & Big Kahuna OG (OFFICIAL VIDEO)

Fly Anakin • 292K views
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Fly Anakin - Affirmations Feat. Pink Siifu (Official Video)

Fly Anakin • 160K views
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Outsidigan's Anthem (Official Video)

Fly Anakin • 30K views
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Ghost (feat. Nickelus F)

Fly Anakin • 51K views
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No Dough (Prod. by Madlib) (Official Video)

Fly Anakin • 218K views
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Things Change

Fly Anakin, Demae, & Foisey. • 246K views
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Intrepid (Official Video)

Fly Anakin • 150K views

Playlists by Fly Anakin

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Skinemaxxx

Playlist • Fly Anakin • 1.7K views
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“Frank”

Playlist • Fly Anakin • 992 views

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