Robert Redford, Barbra Streisand & More Actors Who Starred in 2 or More Films That Spawned No. 1 Hot 100 Hits

Robert Redford, who died on Tuesday (Sept. 16) at age 89, accomplished a great deal in his long career. His obits mentioned his many starring roles, his work as a respected director, his role in founding the Sundance Film Festival, his environmental activism and much more. But most missed this fun factoid – He starred in three films that spawned No. 1 hits on the Billboard Hot 100: Butch Cassidy and the Sundance Kid, The Way We Were and Up Close & Personal.

The songs from those films — pop classics all — were, respectively, B.J. Thomas’ “Raindrops Keep Fallin’ on My Head,” Barbra Streisand’s “The Way We Were” and Celine Dion’s “Because You Loved Me.” The first two of these songs won Oscars for best original song. The third, probably Diane Warren’s finest song, was nominated.

Redford was one of just a handful of performers to star in three films that spawned No. 1 hits. The Beatles, Richard Gere and Emilio Estevez are also in this little club.  

The key phrase there is “star in,” not just “appear in.” Tom Cruise starred in two films that spawned No. 1 hits – Top Gun (Berlin’s “Take My Breath Away”) and Cocktail (Bobby McFerrin’s “Don’t Worry Be Happy”). Cruise also appeared in a third – Endless Love (Diana Ross & Lionel Richie’s “Endless Love”), but that’s not the same thing as starring in a film. (Cruise was just 18 when the film, his first, was shot in 1980.)

The great character actor Hector Elizondo appeared in both American Gigolo and Pretty Woman, but few were buying tickets to see the latest Hector Elizondo film. Such actors can help make a film a success, but a star is someone who makes you decide to see the film in the first place.

So, how did I decide who starred in or just appeared in a film? I looked at the theatrical release posters for the films to see who was in the key art and whose names appeared high on the posters. It got a little tricky in the case of films with ensemble casts, such as those Brat Pack films of the 1980s, but if they were positioned as co-equal leads, I took them.

Others who appeared in two films that spawned No. 1 singles, but who didn’t meet the above definition of starring in both films, include: Kim Basinger (8 Mile, Ready to Wear); Stockard Channing (Grease, Up Close & Personal); John Gielgud (Arthur, Chariots of Fire); Val Kilmer (Top Gun, Batman Forever); Martin Lawrence (Boomerang, Bad Boys II); Bill Murray (Ghostbusters, Charlie’s Angels); Julia Roberts (Pretty Woman, Ready to Wear); Katharine Ross (The Graduate, Butch Cassidy and the Sundance Kid); and Christian Slater (Young Guns II, Robin Hood: Prince of Thieves).

Here’s a list of actors who starred in two or more films that spawned No. 1 hits on the Hot 100. The actors that starred in three such films are listed first, followed by the actors who starred in two. Ties are listed in alphabetical order by last name.