Drew kicks off season two at the Paramount Lot in Los Angeles, with "The Morning Show" star Jennifer Aniston. Plus, "Let's Make A Deal" host Wayne Brady stops by and put Drew and Jennifer's game skills to the test, as they play to raise funds for Wagmor Pets Dog Rescue. Then, in an all-new Drew-Gooder, Drew shines a spotlight on Dolores Sheen, a.k.a. Aunt Dolores, who has spent the last 50 years educating children from underserved communities in Los Angeles. Plus, Drew is celebrating hometown pride, all week long, with viewers sharing tours of what makes their hometown so special and unique, including today's hometown spirit tour of Boston.