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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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EL DORADO E
A-Reece
3
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When Thugs Cry E
Fly Anakin
4
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My N*gga E
Fly Anakin
5
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Tha Divide (feat. Zelooperz, MAVI & Koncept Jack$on) E
Pink Siifu

Albums

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Forever Dream: Night Shift

2026
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Skinemaxxx (Side A)

2023
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FlySiifu's

2020
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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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Skinemaxxx (Side B)

2023
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$mokebreak

2021

Singles & EPs

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Tear It Off

Single • 2026
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The Times

Single • 2025
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Things Change

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

Single • 2025
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Intrepid

Single • 2023

Videos

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No Dough (Prod. by Madlib) (Official Video)

Fly Anakin • 220K views
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Black Be The Source (feat. Pink Siifu & Billz Egypt) (Officia...

Fly Anakin • 149K views
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Happiness (feat. Henny L.O. & $ilkMoney)

Fly Anakin • 25K views
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Fly Anakin - Affirmations Feat. Pink Siifu (Official Video)

Fly Anakin • 163K views

Playlists by Fly Anakin

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Skinemaxxx

Playlist • Fly Anakin • 1.8K views
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“Frank”

Playlist • Fly Anakin • 1K views
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(The) Forever Dream: Night Shift

Playlist • Fly Anakin • 5 views

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