1. 

   11 days ago

   DABABY: Sundae Conversation with Caleb Pressley

   Sundae Conversation
2. 

   9 months ago

   RICK ROSS: Sundae Conversation with Caleb Pressley

   Sundae Conversation
3. 

   9 months ago

   JAMEIS WINSTON: Sundae Conversation with Caleb Pressley

   Sundae Conversation
4. 

   5 months ago

   KAI CENAT: Sundae Conversation with Caleb Pressley

   Sundae Conversation
5. 

   7 months ago

   CARDI B: Sundae Conversation with Caleb Pressley

   Sundae Conversation
6. 

   6 months ago

   FUNNY MARCO: Sundae Conversation with Caleb Pressley

   Sundae Conversation
7. 

   8 months ago

   THAT MEXICAN OT: Sundae Conversation with Caleb Pressley

   Sundae Conversation
8. 

   1 month ago

   FIREBOY DML: Sundae Conversation with Caleb Pressley

   Sundae Conversation
9. 

   6 months ago

   SKETCH: Sundae Conversation with Caleb Pressley

   Sundae Conversation
10. 

    2 months ago

    QUINN EWERS: Sundae Conversation with Caleb Pressley

    Sundae Conversation
11. 

    2 months ago

    KEVIN O'CONNELL: Sundae Conversation with Caleb Pressley

    Sundae Conversation
12. 

    1 month ago

    GRADEY DICK: Sundae Conversation with Caleb Pressley

    Sundae Conversation
13. 

    1 month ago

    BIGXTHAPLUG: Sundae Conversation with Caleb Pressley

    Sundae Conversation
14. 

    19 days ago

    MATTY MATHESON: Sundae Conversation with Caleb Pressley

    Sundae Conversation
15. 

    4 months ago

    HARDY: Sundae Conversation with Caleb Pressley

    Sundae Conversation
16. 

    7 months ago

    BROOKS KOEPKA: Sundae Conversation with Caleb Pressley

    Sundae Conversation
17. 

    8 months ago

    KYGO: Sundae Conversation with Caleb Pressley

    barstoolsports
18. 

    2 years ago

    Hasbulla & Caleb Pressley meet up

    REDCACHE
19. 

    8 months ago

    Caleb Pressley's Guests CAN'T Stop Laughing pt. 2

    comedyapex
20. 

    1 month ago

    Caleb Pressley is Reunited with His Arch Enemy | The Yak 10-10-24

    Barstool Yak
21. 

    1 year ago

    Drake and Caleb Pressley interview 😭 #shorts

    rreeces
22. 

    1 year ago

    Drake and Caleb Pressley interview 😭 #shorts

    rreeces