$31.21 including tip and delivery for me in Manhattan. I just priced a random pizza from dominos.com with three ingredients and that came out to $26.38 total, so it sounds like the roulette.pizza prices are a result of them adding a lot of toppings to a pizza (5-6?). You can also get a large pie from a place that's truly excellent (like Joe's Pizza) for less than $30, though I don't know if they deliver.

It's definitely not worth it from a price perspective. The best deal at the moment, if ordered directly from Dominos, appears to be 2 Medium 1-Topping Pizzas, 16 Piece Parmesan Bread Bites, 8 Piece Cinnamon Twists, a 2 Liter of Coke, and a $1 donation to St. Jude for $19.99.

roulette.pizza could use some better price-optimization mechanics, like fewer toppings (it's really diminishing returns past the first few), picking a pre-made pizza randomly, or even being able to randomly order whatever Domino's deal of the moment happens to be, like that St. Jude offer.

Unsurprising for Dominos. In the UK their pizzas are consistently 2x the cost of a good takeaway pizza, or 3-4x the price of something equivalent to Dominos in quality. They only exist because of brand recognition.

I don't know where it gets ordered from, but a place in my town has pizzas that are about $30-$40 and they're worth it. For one, they're just amazing pizza, made by an amazing local entrepreneur, with a cool little pizza shop. For two, it's a meal out for 3 or 4 (they don't actually deliver), which isn't a bad price to eat out.

If it's Dominos, then I feel your pain.