Jack Dempseys would be happier in at least a 75 gallon tank, especially if you have two. If they are both males, they can each stake out a territory and have enough space not to kill each other. Or you could get a breeding pair and raise fry.
Oscars need 75 gallons at minimum as well to be happy. With a common pleco you would need to go up to a 125 because they get huge (18-24 inches). An oscar and a plec can get along just fine because there is no competition. Plecos are bottom dwellers, oscars prefer the middle.
If you can afford a big enough tank, by all means go for it. All those fish are amazingly gorgeous and its a lot of fun to watch them grow. If not, I would aim for fish that don't get as large. Happy fish keeping!