JazzInToronto’s All That Cabaret presents

Jeff Madden – Sinatra In Love

Monday September 28th, 2026
Hugh’s Room, 296 Broadview Ave, Toronto

Sinatra in Love is a romantic new cabaret celebrating the timeless songs of Frank Sinatra by award-winning actor/singer Jeff Madden. You’ll be swept away by nostalgia, heartfelt story-telling and the unforgettable melodies that made Sinatra an icon. With his rich vocals, effortless charm and acclaimed storytelling, Jeff takes audiences on a moving musical journey through every stage of love, from first glance and flirtation to passion, heartbreak and new beginnings. Featuring Sinatra’s most beloved classics alongside rare musical gems, Sinatra in Love is an elegant, stylish and deeply entertaining evening that proves why these timeless songs continue to resonate across generations.

Jeff Madden is a Toronto-based singer, actor and educator, and a leading member of this country’s musical theatre scene. An original Canadian cast member of Mirvish’s Come From Away, Jeff performed the role of “Kevin T & others” more than 700 times between 2018-2025. He also played “Claude and others” in the Gander, Newfoundland production of that show. Jeff is best known as Canada’s first “Frankie Valli”, starring in the Canadian premiere of Jersey Boys, winning the coveted Dora Award for Outstanding Performance in a Musica’. Jeff performed that vocally grueling role 700 times in Toronto and across Australia between 2008-2013. He has recently created a dynamic show with Adrian Marchuk, called How We Got To Jersey – A Tale Of Two Frankies, which has delighted audiences across Ontario, and will play the Theatre Orangeville this September 25-27.

Other Toronto theatre appearances include Shrek, Rock of Ages, Forever Plaid, Echoes, and I Love You Because (Dora Nomination). Elsewhere, Jeff played the lead role of Lawrence Jameson in Dirty Rotten Scoundrels in BC and appeared at the prestigious Shaw Festival for eight consecutive seasons, playing roles in Wonderful Town, Tristan, Belle Moral, Happy End, Floyd Collins and many more.

Jeff has appeared on TV’s Terminal List, Murdoch Mysteries, Mayday, Accused and The Parker-Andersons, recorded voice-over work, created a series of cabaret shows called “My Life In Song”, and recorded two CDs of musical theatre and pop songs. Jeff is a competent piano and trumpet player, holds a Master of Education degree from U of T, and teaches acting and singing privately in addition to being a part-time faculty member at Sheridan and Randolph Colleges off and on for many years. See him live at Hugh’s Room on Monday September 28.