I've done it a few times and gotten away with it, but that was probably just luck.
Now for anything further than a block or two I use a tow bar, like the kind used when dragging your car behind your motorhome so you'll have something to drive when you get there. No second driver necessary.
Mine has flanges sticking out sideways that I can lash securely to the bumper with ratchet straps, at least on my 1980 Buick whose bumper is amenable to that sort of thing, rather than bolting it on for a one-off recovery/dragging it to the shop. One of these days I'll have to build/buy brackets to hook my other vehicles with it.
I also connect a heavy chain between the frames of both vehicles and wrap it around the tow bar. If anything or everything else fails, the chain will prevent my rig from going out of control or becoming a problem for others...I'll just have to stop and put it back together. Nothing like that has ever happened.
Of course it's not a 65mph highway rig even with that chain; backroads/moderate speeds only!
A chain is more appropriate for that type of job. The strap is important when recovering a stuck vehicle because you're gonna break it whether it's a chain or a strap, and you don't want a chain slinging itself back at you when it snaps. To tow an unstuck vehicle you're probably not gonna snap the chain.Anyway, not having my power brakes and a short tow strap to go the last half mile to the shop (lousy red light and rush traffic or I would have made it with clutchless shifting but for the stop), i did not have a good feel for braking power so basically did overkill and broke the guys strap, so we tied it on this time and go there with a bit less brake effort, but those brake pads got hot enough to smell.
Also, you get better at de-powered brakes (and steering) with practice - and IMO everyone should periodically practice (under controlled conditions) by putting it in neutral and killing the engine so you'll be able to handle a moving car with a stalled engine in an emergency.