There were all kinds of music events available to Washingtonians over the Memorial Day weekend, but a special group of friends were on hand for the debut performance of an unlikely country-and-Western crooner: Verlin Jack, who sang songs about his life, including a memorable drinking bout in Cuba with Fidel Castro. Jack is more commonly known as Jim Kimsey, cofounder of AOL. In Verlin Jack mode, Kimsey was Western from the top of his head to the tips of his toes: black shirt and jeans, black alligator boots, and a big ol’ belt buckle bedecked with a large V. He was backed by his band, the Hired Assassins.

As singers are apt to do, between songs he told stories, including a corker about Fidel Castro. He said he’d had a couple of occasions to visit the Cuban leader. “I was told about his dehydration during the day so that he could drink all night. I stayed in my room at the National Hotel and dehydrated all day, so I could out-drink Fidel.” Once they got together it became a mano-a-mano duel to see who would “break the seal” and use the restroom first. “I wish I’d worn a darker shade of trousers,” Kimsey said, and then launched into a tune dedicated to Castro, with the lyrics, “I’m gonna wait you out.”

Guests filled the tented penthouse terrace outside Kimsey’s office on Pennsylvania Avenue adjacent to the White House. Among Kimsey’s assorted older friends was Ronan Farrow, the 24-year-old offspring of Woody Allen and Mia Farrow. Farrow is a youth adviser to Secretary of State Hillary Clinton and knows Kimsey through their work with Refugees International; the two collaborated on several tunes, including the one about Castro.

The view was spectacular; ditto the heat. Large fans and pitchers of sangria were on hand, as well as two Southern buffets of ribs, corn pudding, and barbecue chicken.

Verlin started a little tentatively, but by the second and third songs he was in his groove, breaking into a dance with one of his backup singers. Most of the tunes were about drinkin’, lovin’, and workin’, plus a couple of Leonard Cohen covers. Alas, nothing about owning the most expensive house in the metro area! Eventually he called up his “lunch buddies” to join him—a chorus of middle-aged men in sports shirts warbling “That’s Amore,” the only non-Western song in the playlist. But then, Kimsey’s friends know that as much as he channels Verlin Jack, there’s a side of him that’s Dean Martin, too.