Lol Dileep's strong phase was like 2000 to 2006. That's it. I mean that's his peak. He's stuck in certain image (boy next door). You can basically guess the formulaic structure of his movies ("stock theernu"). But still, he's better than Jayaram. Now that he's 50+, it will be hard to do that "boy next door" thing. Also, the recent controversy he's been in only damages his image.
Post 2006, the only decent films he did were the likes of Marykkundoru Kunjaadu and Two Countries. And Ramaleela was pretty decent too. (Should My Boss be counted? it's basically a rip-off of the The Proposal)
Even though things like Mayamohini were big commercial hits, the coming generation would only see it the same way we see commercial hits of Nazir from the 60s and 70s.