Frankly Drinking

09/04/2026

New 30th episode just dropped! Features a trio of timeless saloon songs from Sinatra and three delicious and innovative pours from Ironroot Republic. “Texas Torch Song Spectacular” is up on all platforms. Enjoy!

20/03/2026

New episode has dropped! This time, we check out three exceptional tracks from the Chairman’s Capitol Records catalog and three extraordinary pours from Louisville’s Rabbit Hole Distillery. Top shelf stuff on the music side and tasting side. Enjoy!

26/02/2026

Toasting the release of the new movie Elvis Presley in Concert, we’ve just dropped “The Chairman and The King,” a new episode of our Sinatra + bourbon podcast, Frankly Drinking With Friends. This one spotlights the relationship between Elvis and Frank and features three pours from Garrison Brothers. Free and available now wherever you get your podcasts! TCB and ring-a-ding-ding!

22/02/2026

New episode dropping Thursday! Meanwhile, we’ve had recent shows with music by Frank and Dean along with tasty pours from Elijah Craig, Blackened and Corsair. Enjoy!

Frankly Drinking With Friends, the swell Sinatra and bourbon podcast.

06/02/2026

Here’s the tasting lineup for the new Valentine’s episode of Frankly Drinking With Friends! This 27th show features the unlikely pairing of Frank’s romantic tunes and Metallica’s whiskey, Blackened. Also features the debut of a new relationship advice segment, “Frankly Wooing.” Out now and free wherever you go for podcasts. Cheers and happy Friday!

02/02/2026

On the recent episode “So Heavenly,” we talked about how bourbon in partly enjoyed bottles has a way of mellowing and opening up over time. Case in point: this bottle, given to Luke back in 2019. It was opened way back then and has been enjoyed, here and there, over the past few years. The gift-giver came over for a small dinner party on Friday, which seemed like the perfect time to enjoy a bit more from this delightful bottle of K**b Creek! No, it doesn’t age in the bottle but it can become even tastier in a half-empty or, in this case, a nearly empty bottle. What do you think, friends?

25/01/2026

Here’s the innovative tasting lineup from Nashville’s Corsair Distillery for the latest episode of Frankly Drinking With Friends. This one also features music from entertainment legend and longtime Sinatra pal Dean Martin. Stay safe, stay warm and enjoy!

17/01/2026

Cohost Chris is out doing research at Bob Dylan’s bar in Louisville, Kentucky. The Last Refuge. Rough duty, but our man is up to the task!

01/01/2026

Happy New Year, folks! Here’s the tasting lineup for the brand new episode of Frankly Drinking With Friends, the Sinatra and bourbon podcast. Out today on all top podcast platforms! Enjoy! Elijah Craig

10/12/2025

Yep, that’s the bottle lineup for the Christmas episode of our Frankly Drinking With Friends podcast. If you’re not a fan of flavored whiskey, tune in and see how cohost Chris utilized two of these bottles to make a pair of festive cocktails! “Merry Christmas, Baby!” is free and out now on all platforms. Cheers!

25/11/2025

https://www.appenmedia.com/milton/bourbon-and-sinatra-podcast-honors-two-of-america-s-best/article_7facc248-4079-4bd6-891b-c746c5d57662.html

Luke Boggs and Chris Reynolds need just three songs and three pours of bourbon to record an episode of their podcast devoted to Frank Sinatra and America’s native spirit.

14/11/2025

For the Thanksgiving episode of Frankly Drinking With Friends, we visit Denver’s Laws Whiskey House and check out three top tracks from Sinatra’s Capitol Records career. Dylan, Redford, U2 and George P. Shultz pop up along the way. Out now wherever you get podcasts. Enjoy!