How about Jimmy Buffet, Aaron Tippen, Alan Jackson, David Lee Roth, Craig Ferguson Kurt Russell, and Patrick Swayze who are and or were very accomplished pilots with multi, commercial, as well as instrument ratings. This list includes singers as well as actors but still sticks to the point of well-recognized serious pilots. Several of these also have their own private airports. Additionally you have Dennis and Randy Quaid, Angelina Jolie, and Lorenzo Lamas. If you want to expand to other celebrity genres you have golfers and race car drivers such as Arnold Palmer, Phil Mickelson, Mark Martin, Jack Roush (car owner), Matt Kennseth, Carl Edwards, Greg Biffle, Kyle Petty, and Bill Elliot.
Ooops, sorry for the repeats. Got distracted by the other half who wanted to know what I was wasting my time on today!