When my son was down to his final decision - between Alabama and Ole Miss - he preferred the academic program at Alabama but wished so much that Tuscaloosa had a Square. He almost chose Ole Miss just for the Square - its quirkiness, charm, bookstores, that unique artsy feel, some place cool and fun to go on the weekends. Tuscaloosa does not offer anything like that at all. Not even a great coffee house like High Point in the Square. Closest thing that Tuscaloosa has is a Starbucks and my son is not a fan of Starbucks.
The historic Bama Theatre offers some independent films, and maybe that will satisfy your son, and is within walking distance.
Having lived in the San Francisco Bay Area for many years, and taken advantage of all that area has to offer, as well as living in an urban city in the Northeast before coming to Florida, I think I understand what you are looking for and Tuscaloosa does not provide any of that. Tuscaloosa is not a bustling urban city. Birmingham is the closest to that in the state, but, of course, a good hour away (though an easy drive.)
I think the school has grown so fast that there has not been enough time to develop the kinds of amenities that one might expect would surround a school as large as Alabama. You don’t have to go too far away from the campus to discover that most of Tuscaloosa is still quite poor and many areas still in disarray due to tornadoes. There is a lot of new retail, even an Aldis (great news for a college student’s budget, and more freedom from the expensive Publix), and a Fresh Market, but nothing new to do around there. Other than a handful of good restaurants, the Strip, where so many students spend their Fridays, is just one bar after another. Booze is the entertainment of choice. If your student is not interested in drinking parties, as my son is not, then Fridays are open for heading away from campus to eat out and maybe going to see one of the plays or concerts offered via the university’s Theatre and Dance and Music departments. Of course, there is football.
That said, you should really visit. Tuscaloosa has a lot going for it. Definitely larger than Oxford, but with an equally beautiful, but larger, campus. Given the scholarship money available at both schools, I would highly recommend trying to get to Tuscaloosa for a visit so your son can see for himself.
And while you are there, make sure to eat at Los Tarascos down on Skyland (the best Mexican you will find, and I grew up eating the most authentic Mexican food in California, and Los Tarascos beats out many of my favorite hole-in-the-walls out West), GloryBound Gyros downtown (charming and delicious), and Dreamland BBQ (an authentic Tuscaloosa Southern experience)