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| Title | Date published | ||
| Joel McHale | 2021-05-29 | ||
| Jennifer Finney Boylan | 2021-05-22 | ||
| Senator Elizabeth Warren | 2021-05-15 | ||
| Symone | 2021-05-08 | ||
| Tariq Trotter AKA Black Thought from The Roots | 2021-05-01 | ||
| André De Shields | 2021-04-24 | ||
| Michelle Zauner | 2021-04-17 | ||
| Ally Love | 2021-04-10 | ||
| Best of WWDTM April 2021 | 2021-04-03 | ||
| Kemp Powers | 2021-03-27 | ||
| Sam Sifton | 2021-03-20 | ||
| Desus Nice and The Kid Mero | 2021-03-13 | ||
| Jordan Jonas | 2021-03-06 | ||
| Dr. Swati Mohan | 2021-02-27 | ||
| Best of WWDTM February 2020 | 2021-02-20 | ||
| Abby Phillip | 2021-02-13 | ||
| Owen Wilson | 2021-02-06 | ||
| Jen Psaki | 2021-01-30 | ||
| Mandy Patinkin and Kathryn Grody | 2021-01-23 | ||
| Phoebe Bridgers | 2021-01-16 |