CMA Entertainer of the Year winners by year tracks every honoree from Eddy Arnold in 1967 through Lainey Wilson in 2025. Garth Brooks leads with seven trophies across six decades of Nashville history.

Eddy Arnold won the inaugural trophy in 1967. Loretta Lynn broke the gender barrier in 1972 and Charley Pride made history in 1971 on the CMA Entertainer of the Year winners by year list.

Garth Brooks claimed seven Entertainer trophies from 1991 through 2019 on the CMA Entertainer of the Year winners by year roll call. Vince Gill, Alan Jackson, and Brooks and Dunn shared the 1990s spotlight.

Kenny Chesney won four times including a 2006 through 2008 three-peat. Taylor Swift became the youngest winner at age twenty in 2009 on the CMA Entertainer of the Year winners by year ledger.

Luke Bryan won back to back in 2014 and 2015. Garth Brooks returned for three more trophies. George Strait claimed a 2013 victory twenty-three years after his last win on the CMA Entertainer of the Year winners by year list.