WINTER SERIES: 20th CENTURY MUSICAL RABBIT HOLES - Dean Hollin. Starts January 12, 2027

Series Dates: January 12, January 19, January 26, February 2, February 9, February 16, February 23 (Snow Day)

Step right up and tumble down the most delightful of musical rabbit holes! Twentieth Century Musical Rabbit Holes with Dean Hollin is a toe-tapping, eyebrow-raising journey through the songs, stories, and surprising connections that shaped a century of unforgettable music. From Cole Porter’s dazzling name-dropping brilliance to the cultural swagger of the Rat Pack, from holiday classics with unexpected origins to the unsung heroes of the Songbook—and even a few rebellions set to melody—this series peels back the curtain with charm, wit, and a knowing wink. Come curious, leave humming, and prepare to hear the twentieth century the way you’ve never heard it before.

January 12: “THE TOP”

Not merely a cleverly composed “list song”, Cole Porter’s iconic “You’re the Top” – written for 1934’s “Anything Goes” contains more than 60 references to what he and his closest friends considered to be “the top” almost a century ago.  

January 19: “GREAT AMERICAN CHRISTMAS SONGBOOK”

Some of the most beloved and celebrated Christmas/Holiday songs of the last hundred years where composed by American writers – most of which were Jewish. 

January 26: “RAT PACK”

The infamous “Rat Pack” of Las Vegas – led by Frank Sinatra, Dean Martin and Sammy Davis Jr. – began as a group of Hollywood notables led by none other than Humphrey Bogart.  Not merely about song and tomfoolery, the Rat Pack played an important role in social change. 

February 2: “SMALL BUT SIGNIFICANT”

Exploring a bit of the other side of Dean’s 2025 “Heavy-Hitters of the Great American Songbook” series.  The Songbook has a number of smaller contributors whose offerings were significant and remain celebrated. 

February 9: “MUSICALLY-MIGHTIER THAN THE SWORD”

Twentieth Century Broadway offerings weren’t merely for the sake of entertainment – but for political commentary and for speaking out against racial injustice.  Particular lyricists and writers used their songwriting skills to expose the underbelly of America. 

February 16: “BEYOND THE SONGBOOK….”

A question often asked is that of ‘equivalents’ of the composers and lyricists of the G.A.S. – in the decades following the unofficial ending of the Songbook era.  Every generation, and every nation, has its poets – and this final session will visit that detail.

Dean Hollin - Biography

A professional entertainer for over three decades now, Dean has worked in so many areas of the entertainment business including actor/singer on stage, television and film, director, writer, lecturer and emcee/host. It was to assume the position of Artistic and Managing Director of the Gayety Theatre, in 2003, that moved him and his growing family from their hometown of Hamilton to Collingwood. 

Recent stage appearances include Larry Dixon in Tom Thomson’s Wake, which continues to play throughout Ontario, a re-mount of Dean’s 2001 production “Cole-Hearted:  A Musical Portrait of Cole Porter” and in 2024 “Brilliantly Bacharach” a show he co-created with vocalist Sheri Weldon and musician John MacMurchy.  More recently, Dean reprised the role of Frank Sinatra in “Memories of the Rat Pack” as part of The Lighthouse Festival’s 2025 season, in theatres in both Port Dover and Port Colborne.  Tis a show he’s been doing (North American and beyond) since year 2000.    

A passionate authority and speaker about the music of the Great American Songbook, his weekly radio program “Radio Limelite – All Things Great American Songbook” is part of Big Band Sunday Night on Zoomer Radio AM 740, Sundays from 7pm to midnight.  Additionally, he hosts “Breakfast Classics” on The New Classical FM, Saturday and Sunday mornings, 6am to 10am. 

His website is deanhollin.com