Gary Cooper was paid more than $150,000 (in today's money) to endorse American Tobacco's Lucky Strike brand in 1937 and 1938. By the late 1940s, he was appearing in advertising for Chesterfield (Liggett & Myers, now an Altria brand).
A quick history of Hollywood’s tobacco deals
Look up studios and stars in tobacco company records
More tobacco ads in Stanford School of Medicine’s colorful collection