The Rollout Show fell apart when they had a big fight a few months ago and fell out. Real talk though, the show was about 2 hours a day, 3x a week so I literally got back 6-7 hours a week.
Currently, I still listen to a few podcasts:
Ebro in the AM: Good pop culture morning show with some wit and comedy. It is meta because they are far enough removed to not take the celebrity stuff seriously and they all have interesting personalities and discussions on race and dating in an accessible way
Improper Etiquette: A popular female radio DJ and a popular clothing founder talk about dating in NYC. Sounds boring but they talk about female things in a way that males can appreciate. Listeners write in with crazy sex stories and one of the host used to do too much drugs and have mental breakdowns so the stories are pretty interesting
Drink Champs is always a good listen as well