So much "open endedness" in OP's question? "Best" for what? If "shooting" involves going to a range and plunking at targets being over-watched by a range boss, then I suppose the answer would be very different than if the young fellow is going to be out thinning out gophers in the pasture behind the barn. Has he been shooting at sparrows and magpies with a pellet gun since he was 8, or is this going to be his first "shooting on his own" experience? Is this going to be an understudy rifle for a few years, until he goes deer hunting with a larger cartridge?
The first .22 I used was my Dad's Cooey 60 - a bolt action. The first .22 that I bought (in my early 20's) was a Nylon 76, then traded that for a Ruger 10/22. My son's first .22 was a bolt action single shot Lakefield, which turns out also to be his son's first .22. It is now outgrown by both - my son had my 10/22 for several years, but it is back with me now - he has a lot more fun with an aperture sighted Win 9422 in the gopher patch, and his son just handed back the old Lakefield, and left with a CZ Silhouette, with a Meuller 4.5-14x40 scope on it. For my own use, besides the 10/22 that now wears an aperture sight set, I have a very nice Cooey 39, a Husqvarna 155A, a Ruger 77/22 22 Mag, a Ruger 96/22 22 Mag, and a Nylon 66, besides the .22 barrel in the Savage 24C. My grandkids with me at the shooting table use all of them - when they go for a walk, they take a manual action - bolt or hammer, and almost always a single shot.
My latest two purchases were both .22's, but a world apart -second last was a Schultz and Larsen single shot Model 61 "free rifle" - 15 pounds of unbelievable "goodness", the "old school" way (or at least as good as 1960 was!!) Last one is the opposite - a CZ Scout with the single shot loading platform plus a couple for 5 round mags. Probably should have bought this one 20 years ago - doing it this way, I am sure I get to pay 2 or 3 times what they used to cost, but I could not afford them at the time. And previous poster is correct - not many folks will cough up $1,000 or more for even one .22 and scope, so the "hands-on" experience can be very different...