Each time I go to Cadillac Lounge I get confused - sometimes the place feels very familiar, at other times everything seems new. Sometimes it feels casual, sometimes uptight. I guess that's because 905ers are increasingly coming to Parkdale? Or maybe its the hipsters. I am not so certain.
What I am certain is that the bar has great beers, bartenders who are willing to chat and their patio is absolutely gorgeous (well, patios, by the mere virtue of their existence, are usually fab). The interior decor is a bit old school and yes there is a Cadillac seat as well, try to grab it. Can't miss the noticeable neon sign outside!
I've tasted a thing or two from their menu and the food was ok-ish (however on every occasion that I ordered soup of the day, it tasted like nothing but salt to me). The food was overpriced (for the quality) too, but then I don't come to a bar expecting great food.
Stick to the beers (or other alcoholic drinks), and come on a friday or saturday night for live music. That's guaranteed fun.