A visit to the new WSKY Lounge in Deep Deuce is a trip back in time to when its home, the Littlepage Building, hosted jazz greats Charlie Christian, Duke Ellington and Count Basie, the Oklahoma City Blue Devils, crooner Nat King Cole, boxer Joe Louis and baseball legend Jackie Robinson.
The vibe is upscale yet relaxed, with bartenders selling classic cocktails just a few feet away from the city's only walk-in cigar humidor. Classic jazz fills the room.
For downtown young professionals like Gentry McKeown, WSKY is a long-sought replacement for Maker's Cigar Lounge, a much-beloved hangout in Bricktown that closed two years after it fell behind remitting sales taxes to the Oklahoma Tax Commission.
“There is something classy about having a cigar bar, a place that allows that,” McKeown said. “I remember when there was really nothing in Deep Deuce at all. WSKY brings a lot of class to the area.”
The mood is exactly as intended by owner Jarrod Holley, who opened WSKY Lounge with partners John Fryrear, an investment banker, and Dewayne Poor, a medical services and supplies executive.
The dream of opening an upscale cigar bar started as Holley, previously a cigar store manager, struck up a friendship with Fryrear.
“We had other businesses together, and we decided to open a cigar bar,” Holley said.
With the closing of Makers, Holley said, the city lost a place where people could visit, smoke and enjoy conversation over drinks. Holley, Fryrear and Poor, meanwhile, share a mutual love of cigars and whiskey — one that has included travels throughout the United States and to as far away as Scotland.
The men patiently searched for just the right spot to open their own cigar and whiskey lounge.
“We didn't want to be in Bricktown, but we did want to be downtown,” Holley said. “We didn't want the hustle and bustle, paying for parking, walking through the crowds. We wanted it to be a neighborhood bar.”
The Littlepage Building, 228 NE 2, was renovated, briefly occupied by a clock sales firm, then remodeled for Sage, a restaurant opened by the building's owners that closed in 2011 after a two-year run. A French restaurant operator then remodeled the space only to never open for business.