For years, I’ve been an enthusiastic fan of bourbon and Frank Sinatra. In 2024, I launched Frankly Drinking With Friends, a podcast toasting these two American classics.
So, what’s the story? Our family moved to Alpharetta when I was a kid. Back then, the nearest movie theaters were in Roswell, and only pickup trucks seemed to travel north of Holcomb Bridge on 400. After graduating from Milton, I earned a history degree at the University of Georgia and later built a career in executive speechwriting.
My Sinatra fandom was sparked by a Rolling Stone review of 1990’s The Capitol Years, a three-CD retrospective. Ol’ Blue Eyes soon found his place in a college music collection heavy on U2, REM and The Beatles, and I found myself listening to Sinatra while relaxing, ironing or prepping for a night on the town.
From the start, I’ve been captivated by Sinatra’s peerless vocals, the music’s hard-swinging swagger and the elevated artistry of the songwriting. There’s something about this mid-century pop music—written, arranged and performed by the very best—that really appeals to me. These are recordings with style and class, brimming with post-war optimism.
My taste for bourbon came later. In college, sad to say, my drinking consisted mostly of wine coolers, cheap beer and rum and Cokes, made with a bottle of Bacardi 151 socked away in my Russell Hall dresser.
At 21, I bought my first whiskey—a pocket bottle of Jack Daniel’s—for an all-night meeting of UGA’s storied debate club, The Demosthenian Literary Society. A year later, visiting my future wife’s family in Louisville, I ordered my first bourbon at Churchill Downs. Seemed like the right call at the home of the Kentucky Derby.
Around 2008, my friends and I embraced tasty brown liquor and never looked back. Early on, I kept a bottle or two in the pantry next to the cereal. The bottles have since multiplied and moved to the basement.
When I decided to start Frankly Drinking With Friends, I knew Sinatra’s catalog and story. With bourbon, I was just a longtime fan. I needed a cohost with serious bourbon chops. Fate (and Google) led me to Chris Reynolds, an Atlanta businessman who teaches whiskey-tasting classes for fun.
Two weeks after meeting, we recorded our first episode with music from Sinatra’s Capitol Records career and pours from Frank’s favorite brand, Jack Daniel’s. (He was buried with a bottle.)
Two years later, we’re cohosts and friends. Once a month, we record two shows in an evening. I choose the music; Chris picks the pours. Three tunes and three tastings per episode. (These are small pours, folks!)
To date, we’ve released 30 episodes and attracted listeners from around the globe. We keep things light and fun, which people seem to appreciate. To be sure, we are enjoying ourselves. And why not? To my mind, few things in life can top friends sharing the sublime delights of curious conversation, fine drink and great music.
The Sinatra and bourbon podcast, Frankly Drinking With Friends, is free and available on Apple Podcasts, Spotify and other platforms.