1. Jason Sudeikis
Then: He was a cast member on Saturday Night Live.
Now: He won the Emmy for Outstanding Lead Actor in a Comedy Series for his portrayal of Ted Lasso on Ted Lasso.
2. Jean Smart
Then: She starred as Shari on Teachers Only.
Now: She won the Emmy for Outstanding Lead Actress in a Comedy Series for her portrayal of Deborah Vance on Hacks.