| 271 | Symone 2021-05-08 |
Play |
| 272 | Tariq Trotter AKA Black Thought from The Roots 2021-05-01 |
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| 273 | André De Shields 2021-04-24 |
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| 274 | Michelle Zauner 2021-04-17 |
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| 275 | Ally Love 2021-04-10 |
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| 276 | Best of WWDTM April 2021 2021-04-03 |
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| 277 | Kemp Powers 2021-03-27 |
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| 278 | Sam Sifton 2021-03-20 |
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| 279 | Desus Nice and The Kid Mero 2021-03-13 |
Play |
| 280 | Jordan Jonas 2021-03-06 |
Play |
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