27. Robert Downey Jr. & Keifer Sutherland

Robert Downey Jr. has had a prolific long-running career in Hollywood. In recent years, he had a lucrative renaissance portraying the fictional billionaire-superhero Tony Stark in the Marvel Cinematic Universe franchise. Before all this newfound fame, he already had a reasonable degree of success in the industry during the 1980s. With this, it is interesting to know that he has built friendships and relationships in the industry, particularly that with 24 star Kiefer Sutherland.

Keifer and Robert started their friendship when they co-starred in the war movie 1969 back in 1988. In an interview Robert did with Howard Stern, he fondly recalls his contrasting relationship with Keifer. His laid-back attitude was the direct opposite of the disciplined work ethic that his co-star had during those days. Nonetheless, they established a long-term friendship and were even dear friends during the relationship he had with actress Sarah Jessica Parker.