Born: 1966 and 1965

While seemingly poles apart in their on-screen personas, Patrick Dempsey and Ben Stiller share a surprising bond beyond the surface. Stiller’s comedic genius, epitomized by characters like Derek Zoolander and Tugg Speedman, contrasts sharply with Dempsey’s portrayal of the charming neurosurgeon, Derek “McDreamy” Shepherd, in Grey’s Anatomy.

Their divergent styles and tones may deceive some into believing they’re of different eras, yet the reality is quite the opposite. Born just two months apart, with Stiller arriving in late 1965 and Dempsey in early 1966, these two luminaries bridge the gap between generations, proving that talent knows no boundaries, not even age.