Episode 01: September 14, 2020 - Adam Sandler Episode 02: September 15, 2020 - Reese Witherspoon Episode 03: September 16, 2020 - Jane Fonda Episode 04: September 17, 2020 - Jonah Larson Episode 05: September 18, 2020 - Billy Porter Episode 06: September 21, 2020 - Paris Hilton Episode 07: September 22, 2020 - Gwyneth Paltrow Episode 08: September 23, 2020 - Stephen Colbert Episode 09: September 24, 2020 - Rosario Dawson Episode 10: September 25, 2020 - Tom Green Episode 11: Adam Sandler and Drew Barrymore Reboot 50 First Dates for 2020 Episode 12: Billy Eichner and Drew Barrymore Play Would Drew Barrymore Like That Episode 13: Derrick Barnes and Gordon C. James Celebrate Black Boys and Girls with I Am Every Good Thing Episode 14: Reese Witherspoon Opens Up About Terrifying Young Motherhood Experience Episode 15: Drew Launches The Drew Barrymore Show’s First Episode with Drew’s News Episode 16: The Big Goodbye Drew Gives a Virtual Audience Member a 2021 Hyundai Sonata Limited Episode 17: Drew and Reese Witherspoon Respect the Difference Between Alone and Lonely Episode 18: The Big Goodbye What Inspires Drew Barrymore Episode 20: Drew's News Drew Introduces Kid Correspondent Jonah Larson! Episode 21: Drew's News Empire State Building, Butt Masks Episode 22: Drew's News Meet the Ebony Anglers Episode 23: Drew, Cameron Diaz and Lucy Liu on Becoming Moms Changing Their Outlook on Life Episode 24: Drew’s News Drew Surprises New Jersey Dad Who Started a Food Pantry During the Pandemic Episode 25: Meet the Copening Family Designed by Drew Episode 26: Drew Kicks Off Her First Show with Her Charlie's Angels Sisters Cameron Diaz and Lucy Liu