A movie that wasn't all that great but which perfectly demonstrates what you're talking about is "Dracula 2000." Oddly, it came out in 1999, I think. There's the heroes, one is the young male protagonist, and I recall he's just a thorough wuss. I mean a totally whiny, wimpy, unlikable, pansy. The young woman protagonist was okay, but he was just annoying. I think it might have been Jonny Lee Miller, Sherlock Holmes from the highly mediocre CBS show "Elementary." Then when Dracula finally shows up, it's Gerard Butler, who I've liked in most things I've seen him in. I always root for Gerard Butler, even as Dracula. Even when he's killing people, he's just way more likable, and I remember it was the first time I ever saw a fantasy/horror movie and rooted for the bad guy. I wanted him to kill the young man and I hoped he turned everybody else into vampires. Then they gave him a cool ending which made me like him even more, though I won't give it away, in case you ever do see it. Although I really wouldn't waste my time on it. Butler as Dracula was the only cool thing about it, and that's when I was 20 years old, God only knows how much I'd think it a waste of time now.
"Justified" was a great, great TV show where I found it easy to root for a villain, Boyd Crowder. You never root against the protagonist, Raylan Givens--he's way too likable for that--but it's a clear device of the show to make you never truly root against the recurring antagonist. CH, if you didn't catch that while it was on, I think you'd really like it....it's available on Amazon Prime.
Maybe the most glaring recent example I've seen is the recently concluded FX series "The Americans" where the main characters/protagonists technically are the villains, from our perspective. If you've never seen it, it's about a couple who are Russian spies in the 80's, living in Washington D.C. posing as a typical American family. I found the show very unsettling in its first season, because they are clearly the main characters the show wants you to identify and sympathize with, but because of their views juxtaposed with my own views, it was nearly impossible to root for them. It created this cool turmoil that I think teh show means to evoke from the viewer. But that's constantly balanced against how likable they are and how you don't want bad things to happen to them personally, you just don't want them to achieve their goals. It was brilliant. By the second season, things settled down emotionally for me--you get more comfortable with rooting for people who's ultimate ends are at odds with your own--and you just relax into it. The show makes them that sympathetic, and it works that well. It's genius. Also available on Amazon Prime, for those who haven't watched it.
