20. Kris Kristofferson

Kris Kristofferson built his reputation as a prolific songwriter and influential voice in country music, penning classics that resonate to this day. His transition to acting was marked by a rugged screen presence, showcased in his starring role opposite Barbra Streisand in A Star Is Born (1976) and as the stoic Whistler in the Blade film series. Kristofferson’s authentic, weathered charm helped him carve out a respected place in Hollywood, proving his talents were not confined to music alone. Read more about his multifaceted career at Britannica.