When I take a booked private car back and forth to the airport (about an hour) I don't really have an issue. Sometimes the driver is chattier. Sometimes I'm chattier. Probably (likely) more expensive than an Uber would be but 100% reliable even at zero-dark-thirty times. Never had a real issue of any sort.
Shared van services got ridiculous sometimes and then I had a couple of incidents related to driving/parking at the airport (like a 10pm cold weather flat). So I just started using a car service at a new job (I think) and the company never flinched. Now--especially as I'm usually taking longer but fewer air trips even if it's usually on my own nickel these days--just keep doing so.
Uber Black provides a similar experience, or at least it used to (haven't used it in many years). I think it's a matter of having professional drivers, where there's an expectation that their customer/client isn't there to socialize, and their job is to drive, and that's it. It's more of a "high class" thing, for lack of a better term.
(IIRC when Uber first started, before UberX, their driver pool was essentially just this sort: people who drove for private car services.)