“None of Apple’s films have done well,” Stephen Galloway, the dean of Dodge College of Film and Media Arts, said in an interview. “Financially, you might think it doesn’t matter. This is a company worth $3.3 trillion. But psychologically, it does.

“Apple’s brand is quality, cutting-edge, sleek, refined, forward-looking, and so now you’re tarnishing that brand with what seems like an old-fashioned, not-relevant, not-part-of-the-zeitgeist slate.”

Apple, which declined to comment for this article, is not alone in its box office struggles. This year has seen some really big hits (“Inside Out 2,” “Deadpool & Wolverine”) and some notable misfires (“The Fall Guy,” “Furiosa: A Mad Max Saga”). And Apple has seen some of its films perform well in streaming.

This month, it released “The Instigators,” with Matt Damon and Casey Affleck, on Apple TV+ after one week of a limited theatrical release. The film helped the streaming service add about 50,000 subscribers, more than the number “Napoleon” accounted for when it was released last year, according to the data firm Parrot Analytics. Another data firm, Luminate, reported that “The Instigators,” which was directed by Doug Liman, was the most-watched streaming film across all platforms during its first week of release.

Apple does not publicly disclose subscriber or viewing numbers.

Apple’s entertainment programming is overseen by Zack Van Amburg and Jamie Erlicht, who both had decades of experience running Sony Television before joining the company in 2017. The film business is run by Mr. Dentler, a former programmer at the SXSW Film Festival who joined Apple in 2012.