Thought-provoking, interesting cast, and high production values, and bonus points if it has political elements. Alright, let me think...
Off the top of my head, the first shows I'd recommend are Ghost in the Shell: Stand Alone Complex and Ergo Proxy. Of the two, I think Stand Alone Complex is a stronger recommendation because it has a bigger cast and better production value. Ergo Proxy is the more thought-provoking of the two, but its slow pacing isn't for everyone. Both are semi-episodic cyberpunk mystery series, so take your pick.
I see you have Ping Pong on your plan-to-watch list. If the wacky art style doesn't bother you, it's an excellent watch. It has a really great cast and plenty of interesting themes, and the technical aspects are all off the charts (assuming, like I said, the art doesn't turn you off). There isn't a political element, unfortunately, but it's one of the best anime out there. And short, too.
You also started Gurren Lagann recently. That definitely fits a lot of your criteria. It's not the most thought-provoking show out there, but it's deceptively intelligent and a lot of fun. I've always thought that it and Steins;Gate share a similar approach to character writing, so hopefully it'll impress you there. It takes a little while to reveal its true colors, but the final arc is definitely a worthwhile payoff. There's a political element, but it's rather small.
And as for manga, 20th Century Boys is a surefire recommendation.
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Off the top of my head, the first shows I'd recommend are Ghost in the Shell: Stand Alone Complex and Ergo Proxy. Of the two, I think Stand Alone Complex is a stronger recommendation because it has a bigger cast and better production value. Ergo Proxy is the more thought-provoking of the two, but its slow pacing isn't for everyone. Both are semi-episodic cyberpunk mystery series, so take your pick.
I see you have Ping Pong on your plan-to-watch list. If the wacky art style doesn't bother you, it's an excellent watch. It has a really great cast and plenty of interesting themes, and the technical aspects are all off the charts (assuming, like I said, the art doesn't turn you off). There isn't a political element, unfortunately, but it's one of the best anime out there. And short, too.
You also started Gurren Lagann recently. That definitely fits a lot of your criteria. It's not the most thought-provoking show out there, but it's deceptively intelligent and a lot of fun. I've always thought that it and Steins;Gate share a similar approach to character writing, so hopefully it'll impress you there. It takes a little while to reveal its true colors, but the final arc is definitely a worthwhile payoff. There's a political element, but it's rather small.
And as for manga, 20th Century Boys is a surefire recommendation.
Hope you find one of these enjoyable!
Your profile says you're looking for recommendations, huh? I've got plenty! What kind of things do you generally look for in a series?