I’m not that familiar with this actor’s work. What’s this referring to?
But wait! There’s more! Not a synchronicity because I saw these a couple of days apart, but nearly the same joke, and I definitely don’t get this one, either.
More Cultural References I Don’t Get
Comics I Don't Understand 
There was a time when Jeremy Renner was in everything. That was a few years back.
And in the second part, Nathan Fielder [shouldn’t they have gone with Fiedler?] does a novelty/comedy program called “The Rehearsal” where he enables people to practice awkward encounters they’re anticipating, by setting up pre-enactments (as it were) with actors. That may be a bit inaccurate because I only saw about half of one episode; but it was in the entertainment-news recently for some reason, probably a renewal, and there were descriptions that partly lodged in my brain.
Also the idea of treating an actor as something predicted in the weather report. Bolling has other eccentric “strips” using celebrities, usually as a caricature that deliberately doesn’t match the artwork: Phil Collins, I think Tom Cruise, and some time ago, the Ghost of James Caan appearing to the annoyance of the still-alive James Caan.