I'm selfishly almost reluctant to add another positive review, lest this gem become too popular!
There are three main reasons that Uptown Barber Shop is beyond worthy of five stars (I'll leave any minor downsides to the perpetually unsatisfied Yelpers who will inevitably find something to nit pick):
1. The atmosphere.
I've always liked a good old fashioned barber shop that isn't drenched in "hipster-authenticity." This place has that old-school charm, without trying too hard. The second you enter, you feel the day's pace slow, and you are carried back to a simpler time.
2. The people.
Valentino is a great guy and a better barber. He will remember what you like and will expertly get to work while picking up with whatever small talk you left off with the previous time. His style is simple, classy, and quality-centric.
3. The price.
If there are other places that you can get a $20 haircut in Toronto, you'd walk out looking like a mangy tomcat. Here, $20 will get you a clean fade, sharp lines, and a classic look.
BONUS. The cut
Maybe the greates thing about Uptown Barber is that all of the above comes hand in hand with a fantastic haircut (the reason you came here in the first place). I've never walked away disappointed, and I've been here dozens of times!