Jesse Williams as Jackson Avery
First episode (2009): "Invasion" (Season 6, Episode 5)
Latest episode (2020): "Put on a Happy Face" (Season 16, Episode 21)
What he's up to now (2020): Of course, Jesse is still on Grey's playing Jackson Avery, and he's directed three episode. He also appeared on Hulu's Little Fires Everywhere this year.