Lou Beatty, Jr.

James Avery.

Best known for his role as Uncle Phil on Fresh Prince of Bel-Air, he played a judge on Webster. And on Reba. And on 2 Guys, a Girl and a Pizza Place. And on Rescue Me. And in Vengeance Unlimited. And on Murder One. And on LA Law. And on Night Court. And on Valerie. And on Dallas.

He was actually a judge on some show called Pet Star, which I'm guessing is American Idol for dogs.

Morgan Freeman.

Do I really need to make a list?

Judge Roy Snider.

The Simpsons (voiced by Harry Shearer)

James Pickens Jr.

Trifecta!

FBI Deputy Director Alvin Kersh, The X-Files

Principal Robbins, Homeroom

Judge Lucius Pearl, Any Day Now

Principal Lewis.

American Dad (voiced by Kevin Michael Richardson)

Earl Billings.

"Miss Guided" is, actually, surprisingly funny.

Lou Gossett, Jr.

Latest "stern police chief" role is in the as yet unreleased "The Real Catch". 

Greg Hollimon.

Principal Onyx Blackman, Flatpoint High School.

Yaphet Kotto.

I can't think of a role of his that wasn't "stern police chief".

Frankie Faison

Has played approximately 152,346 stern police chiefs and judges.