The founders of the Rainey Day Fund were supporting the artists they loved even before the project had a name. Here are some of the recipients of Rainey Day grants:
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| Birds of Chicago | Chastity Brown | Tré Burt | Antje Duvekot | Izzy Heltai |
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| Kaia Kater | Amythyst Kiah | Miko Marks | Leyla McCalla | Pamela Means |
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| Danni Nicholls | Nickel&Rose | Joy Oladokun | Rissi Palmer | Wild Ponies |
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| Jontavious Willis | Yola | Natalia Zukerman | Indigenous Music Scholarship |
