In recent memory, Jeffrey Richards might be the answer to both questions if you're counting shows and not dollars.
Of the 30 some-odd shows he's produced in the last 12 years, he's had some big financial successes (August, Merchant, Will Ferrell) and some reasonable ones (Glengarry, Speed the Plow, Spring Awakening, Hair, Race) but pretty much all of the others have been money-losers.
So by being as prolific as he is, measuring by shows might merit him both distinctions.
In terms of winners in dollars and/or all-time, I'd guess that Cameron Mackintosh wins hands-down because of his stakes in Cats, Les Miz, Phantom and Saigon. Really Useful/Andrew Lloyd Webber is probably a close second. Hal Prince is definitely in the conversation, but there wasn't a first-class international market then like there is now so it's not really a level playing field.
Also important to distinguish between shows that a producer has put their name on and shows where that person was truly the lead producer. Rudin's track record as a lead producer is pretty incredible, but he still has his name on plenty of shows that lost money.
joined:12/10/04
Posted: 5/5/12 at 09:51am