As popular as The Orville has become since its inception, one criticism has dogged it right from the start - the character's pop culture jokes make absolutely no sense. However, not only does The Orville agree with these criticisms, but in acknowledging them, it actually offers an explanation that justifies them within the show's continuity.
Created by same vein as classic Star Trek, where the lack of futuristic pop culture has led to fan theories about the Federation being a stagnant culture, however in that case, it's at least timeless art that's still being enjoyed.
In 2021's The Orville: Digressions (from David A. Goodman and David Cabeza), fans get to see the alternate reality created by Kelly's younger self learning of her potential future. Without Kelly arguing for Ed Mercer, he never makes Captain, and instead ends up as a poorly-liked First Officer. While being disciplined by his Captain in issue 1, Ed is called out for "the pop culture references that no-one seems to understand but you. Five-hundred-year-old movies and televisions shows that no-one watches anymore, that no-one cares about anymore."
This moment calls out the bizarre idea of random human pop-culture being memorable centuries later, but it also hints at an explanation of sorts for the jokes in the show. This moment presents Ed's use of 21st-Century references as a personal obsession, hinting that it's not that everyone understands these references in the future, but that Ed himself is unnaturally obsessed with the culture of the era. While Kelly and Gordon often make similar jokes in the show, both are also close to Ed in their personal lives, and it makes sense that what fans are actually seeing are three people who share a niche interest, with their combined high ranks establishing this as part of the culture of the ship.
This makes sense given the scenes of Ed recommending 'old' movies to those he's close to, Kelly choosing ancient music for karaoke, and Gordon Malloy's habit of programming the ship's Environmental Simulator with scenarios for other crew to enjoy. It makes sense that The Orville is simply a workplace where everyone has to show interest in the senior crew's 21st-Century obsession - something which The Orville: Digressions makes it clear wouldn't fly on other ships in the fleet. When Gordon says, "We are, without a doubt, the weirdest ship in the fleet," it seems this fixation might be part of the reason why.
Ultimately, The Orville's humor isn't meant to be taken that seriously, but in a curious sci-fi show asking questions about current society through the lens of the future, it's a detail that understandably impacts the immersion of some fans. Happily, The Orville is aware of this, and while its solution may not be perfect, it is perfectly keyed into the show's overall tone as 'workplace sitcom meets speculative fiction.'
