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Among the many accomplishments of Herb Alpert—which include cofounding A&M Records, releasing 28 Billboard-charting albums (including five that reached number one), and being the only artist to top the Billboard Hot 100 as an instrumentalist and as a vocalist—the easy-listening legend has nine original sculptures on permanent display at the Field Museum. But that isn’t even the trumpeter’s most important connection to Chicago: for nearly five decades he’s been married to a local native, Grammy-winning vocalist and former Sérgio Mendes & Brasil ’66 member Lani Hall, who’s joining him for tonight’s show at City Winery. As a musician, Alpert is arguably best known for his time with the group he created in 1962, the Tijuana Brass, an early example of white popular music borrowing Latin sounds for fortune and fame. The Tijuana Brass started as Alpert and the iconic group of session musicians known as the Wrecking Crew. On their debut single, “The Lonely Bull,” they play a lite version of mariachi, complete with corny shouts of “Olé!” As the popularity of the group grew, Alpert assembled a permanent ensemble and moved away from Latin sounds and toward the smooth pop-oriented jazz that would define the rest of his career. Alpert’s warm tone hasn’t diminished over the years, which has allowed him to carve out a solid niche as a jazz player with an infectious sense of joy and playfulness. Hall left Brasil ’66 in 1971, embarking on a solo career that peaked with a Grammy win in 1986 for her album Es Fácil Amar. In the midst of that success, she contracted the Epstein-Barr virus, which led to her retirement from the stage for almost ten years. Since making a return to music in the late 90s, though, she’s expanded her talents—not only recording as a vocalist with Alpert but also working as a producer on a number of their releases. Expect Hall and Alpert’s performance to briefly nod to their most popular moments (they’ve been playing Tijuana Brass and Brasil ’66 medleys as part of their regular sets) as it spans the lengths of their extensive careers. Alpert recently reinterpreted a number of Tijuana Brass classics as lush space-lounge jams for his latest CD, Music Volume 3: Herb Alpert Reimagines the Tijuana Brass, so with any luck you’ll also get to hear some old favorites in delightful new configurations.