Three of a kind

Hourglass
Sundial
Calendar

Three time measuring devices

Manny
Moe
Jack

Pep Boys

Meanwhile, Sandy Duncan stares on, forlornly and monocularly. :frowning:

Andrew Vachss does [del]two[/del] too,

Archibald Leach
Bernard Schwartz
Lucille LeSueur

Three people who have never been in my kitchen.

Plaxico Burress
Michael Vick
O.J. Simpsons

Professional football players who served time in prison

Kevin
Justin
Gary

Three famous men named “Trudeau”

Peter Falk
Sammy Davis Jr.
Thom Yorke
Andrew Vachss
Sandy Duncan

Could have had a Yahtzee!