Before making it big, Ryan Seacrest and Jensen Ackles were just two bachelors living in California. During an appearance on Live With Kelly and Ryan, the Supernatural actor reminisced about when he was roommates with the cohost. At the time, Jensen was still on soap operas and Ryan was just starting out on the radio. While we love the adorable throwback picture they shared, the best part is the woman giving them the side-eye in the background. Hint: it's a famous '90s actress.