How are we defining “rich” here? Cliff and Claire may own their house and some assets, but they still work for income. They might be in the top 5%, or the top 1%, but the curve after that gets considerably steeper.
Joy, now in theaters, is about how the title character (based on Joy Mangano) became a self-made woman through hard work, good ideas, and determination. For most of the movie she’s struggling, but there’s a fairly lengthy sequence near the end showing her as a successful businesswoman who lives in a mansion but is still decent, honest, and hardworking.
Jean Valjean in his guise as M. le Mayor in Les Miserables, perhaps.
Well, in “Tommy Boy,” the Callahan family is rich, but family patriarch Brian Dennehy is portrayed as an admirable guy who made his fortune honestly in the auto parts business, and who genuinely cares for his employees and for the people of Sandusky, Ohio.
“Death of a Salesman” actually does have a character who’s both a wealthy businessman and a decent, hard working individual: Willy’s neighbor Charlie.
Willy seems like proof that the American dream is a hoax, but Charlie shows that even Arthur Miller can’t completely dismiss Horatio Alger.
Just for fun, I looked up current salary figures.
For some reason, they’re all over the place–I have a feeling that different sites may be using different definitions. Payscale.com says that the median lawyer’s salary is about $77,000/year. Medscape.com says that only 10% of ob/gyns earn less that $100,000, with the majority earning over $200,000. For convenience, let’s say $200,000 for Cliff.
So that’s $277,000 per year. The median household income is about $53,000. According to this handy calculator, they would certainly be in the top 3%.
If Cliff was toward the top end of the payscale, they would probably be in the top 1%.
Pursuit of Happyness
Meet Joe Black
Yes, there is a definition problem here. You aren’t rich if you have to work for a living. Arguably, you aren’t really rich if your children have to work for a living.
You can be rich and also hard working, or rich and lazy, or rich and canny, or even rich and well-connected. But if you are poor unless you go to work, you aren’t rich.
I don’t agree with the thesis of the OP. America worships wealth. The Rich are usually Heroes and the Poor are often presented as criminals.
I think the Evil industrialist trope is used sparingly. And usually it is when finally some White Collar Crime is in the the news, such as Enron, Bernie Madoff, or the 2008 collapse.
The Evil Corporation is more common but often the face of the “Evil Corporation” isn’t the CEO but some Middle Manager doing the dirty work.
Sympathetically :
*Babbit
Slaughterhouse -5
Annie?
Les Miserable
*
We are “temporarily embarrassed millionaires.”
And that’s where you lost me. 
Part of the problem is that the sort of work the rich mostly do is exceedingly boring and makes terrible TV.
And I think Annie is a bad example. Daddy Warbucks may take an interest in a poor girl, but how he got his money is described in his name: he’s a war profiteer. He’s a philanthropist, but how many people died to make him rich?
Silicon Valley is a good example. The guys are nerds, but they work hard for their wealth.
I haven’t read all of Jeffrey Archer’s novels, but many of them praise the hardworking well-off. As I recall, As the Crow Flies and Kane and Abel are good examples.
Titan, the biography of John D. Rockefeller, was particularly impressive. The guy may have acted like a dictator, but he worked very hard and pulled himself upward one rung at a time.
Hence the question mark 
My old billionaire boss would work a lot, staying in the office until the wee smalls. What he was working on I don’t know since it wasn’t drumming up business and wasn’t keeping the company afloat. His wife was gorgeous and nice, but for some reason he, an Aspie without the smarts, was avoiding her. At a party I almost asked why she didn’t leave him, but she did a few months later on her own, without me in the role of co-respondent. Darn!
Plantagenet Palliser from Anthony Trollope’s Palliser novels is a wealthy duke, but he is still a very diligent Chancellor (and later Prime Minister).
Good call. Lord Grantham isn’t nearly the frivolous upper-class asshole you’d think he’d be portrayed as. Instead, he’s got a very acute awareness of his position as the employer of all the people of his estate and how his (and his family’s) actions affect them.
Historically the worker/employer relationship has always been a reciprocal one beyond merely the work performed and the wages paid. What we’re seeing now is kind of like a historical swing of the pendulum- on one side you have stuff like company towns, truck systems and debt bondage, and on the other you have today’s almost entirely divorced system, where you’re worth exactly what your paid, no more, no less.
That’s, I think, what a lot of the anger toward the “rich” lately is about- there’s a feeling that the historical compact is broken, and personally, I’d be willing to bet that the angst has grown at about the same rate that people are employed by faceless huge corporations that aren’t invested in their communities.
I mean, if say… Callahan Auto Parts is based in Sandusky, and the vast, vast majority of their employees live in Sandusky and the surrounding areas, they have a certain reciprocal obligation to the community.
But when you work for say… Home Depot, they don’t have any particular obligation to even somewhere as big as Dallas, and will shut stores on a whim and lay hundreds of people off without thinking about it.
Funnily enough, I’ve not seriously watched Downton Abbey, but now it’s over, I’ll buy the boxed set when it comes out and binge-watch it.
Would you prefer that Germany won the war?
My nominee is The Pleasure of His Company, in which Fred Astaire plays a stereotypical idle rich, and Tab Hunter plays a hard-working nouveau riche.
In retrospect, an unfortunate choice to make in creating that character…