Boss S1-S2

Kelsey Grammer

Mayor Tom Kane

Connie Nielsen

Meredith Kane

Hannah Ware

Emma Kane

Jeff Hephner

Ben Zajac

Kathleen Robertson

Kitty O'Neill

Troy Garity

Sam Miller

Rotimi

Darius Morrison

James Vincent Meredith

Alderman Ross

Martin Donovan

Ezra Stone

Mary Hollis Inboden

Jackie

Mary Hollis Inboden

Sentinel Colleague

Mary Hollis Inboden

Sentinal Colleague

Francis Guinan

Governor McCall Cullen

Nicole Forester

Maggie Zajac

Steve Lenz

Phone Monkey

Steve Lenz

Kane's Aide

Daniel J. Travanti

Gerald 'Babe' McGantry

Tony Mockus Sr.

Mayor Rutledge

Jonathan Groff

Ian Todd

Candace C. Edwards

Mona's Assistant

Candace C. Edwards

Monas Assistant

Sanaa Lathan

Mona Fredricks