DMC1 Dante probably had a relatively adventurous and B-action flick lifestyle of kicking demon ass and eating pizza.
DMC2 Dante probably had the hardest life and has now treated it all like a dull job to get through. Something traumatic must have happened to him.
DMC3 Dante was living his best and worst life. The best coming from the fun he had killing demons and saving the world, the worst from losing his brother and him realizing that Sparda's baggage is gonna haunt him forever.
DMC4 Dante just seemed to be the one to go through the motions of watching over a new generation of Sparda lineage.
DMC5 Dante is probably Dante at his lowest, where even he doesn't know what's gonna happen. Exciting, but also terrifying.
DMC anime Dante is him at his most bored, and only doing jobs just for the hell of it.
DmC Dante has probably had the worst life of them all since he was forced to fight demons 24/7 and couldn't pick and chose which he wanted to fight and which he didn't. There was some fun in fighting demons for a good stress reliever but other then that, they were a hassle to deal with. And then he loses his brother and now demons are attacking everyone in real life.