Joe Della Penna

reservationsDine With Us.

Following his nostalgic memoir of last year, “That Christmas Cabaret Show: Make The Yuletide Slay!”, pianist, singer, and comedian JOE DELLA PENNA returns to the Napoleon Room with JAZZ LEGENDS: A Birthday Party Cabaret Celebrating Miles, Trane, Tony, and Jackie

Joe’s first show of 2026 celebrates the centennial of Miles Davis, John Coltrane, and Tony Bennett, and also pays tribute to his greatest mentor on his 95th birthday: educator, composer, and bandleader, Dr. Jackie McLean.

Jazz has always been at the heart of Joe’s music, and he has plenty of funny stories to share about his teachers, his friends and family, and a few encounters with celebrities where he really gets to spill the tea!

JOSEPHINE’S in the NAPOLEON ROOM – Boston’s best professionals and tomorrow’s rising stars singing JAZZ, BROADWAY & MADCAP CABARET! Dinner seating starts at 5:00 pm and the one hour show begins at 6:00 pm. RESERVATIONS strongly recommended.