In 2005 Reagan and Randy smoked their first cigar together to celebrate Reagan's high school graduation. After that first cigar, Reagan and Randy would smoke cigars occasionally on the back porch, or basement of the house, fondly referring to the space as the R & R Cigars. When Reagan went off to college and law school, they would smoke cigars at his apartment, R&R 2.0. R&R became a place for Reagan and Randy to spend time together and have meaningful time together as father and son by sharing a cigar. Tuscloosa had been completely ignored by the cigar industry for almost 5 years by the time Reagan had finished law school.

After Reagan graduated law school in 2011, Randy and Reagan decided to open R&R Cigars in Tuscaloosa, to bring a place to relax and recharge from the daily burdens of the stresses of life. In January of 2012 R&R Cigars opened their doors to the public for the first time. By January 2013 R&R celebrated their first anniversary by having Rocky Patel himself coming to the anniversary party, and setting a south east record for most boxes sold at an event. In May of 2013 R&R Cigars moved to the historic Maxwell House, where R&R currently resides. In 2014 Reagan became the youngest Board Member of the International Premium Cigars and Pipes Retailer Association at the age of 26. Later in 2014, R&R purchased the Maxwell house and Reagan released his cigars, the Black Warrior and Casa de las Estrellas.

In November of 2014 R&R Cigars opened Reagan's White House Bar at the Maxwell house. Striving to be the best whiskey bar in the South East, R&R became Tuscaloosa's only Whiskey Bar. R&R is the only bar in Tuscaloosa with 100 years of Balvenie, 100 years of Macallan, 100 years of Glen Fiddich, 100 years of Highland Park, and 100 years of Flor de Cana rum.