Guest Stars Ray Romano as Hank Rizzoli Matt Lauria as Ryan York Lyndon Smith as Natalie David Denman as Ed Brooks Tyson Ritter as Oliver Rome Matthew Atkinson as Zach Rose Abdoo as Gwen Chambers Jurnee Smollett as Heather Hall Sonya Walger as Meredith Peet Andrew Joseph Barr as Band Member #4 Leonard Jay Jackson as Band Member #5 Ryan Wells Peterson as Band Member #3 VyVy Nguyen as Akio Courtney Grosbeck as Ruby Rizzoli Mark Charran as Tom Dennis L.A. White as Mista Ray Ayanna Berkshire as Caroline Lee Googy Gress as Doug Kevin Linehan as Volunteer #1 Big Leroy Mobley as Campaign Supporter Helen Slayton-Hughes as Edie Algerita Wynn as Woman Jaime Chavez as Shopper Jenna Ryan as Citizen Naomi Taylor as Emma Trevor Hammonds as Campaign Supporter Jordan C.M. Brentley as Boy #2 Michelle Boone as Mom Shawn Kissinger as Boy #1