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Asleep At The Wheel Tour 2025. Altogether, they have won nine grammy. Asleep at the wheel is a grammy award winning american country music group that was formed in paw paw, west virginia and is based in austin, texas. Asleep at the wheel is an american country music group that was formed in paw paw, west virginia, but based in austin, texas. For over fifty years, asleep at the wheelโs ray benson has been traversing the globe as an ambassador of western swing music and introducing its irresistible sound to generation.