The Bobs rocked, and so did the Flying Turns, another of Riverview's six coasters. (I was only there once and loved it.) The "laugh your troubles away" reference comes from the TV commercials with "Two Ton" Baker, who looked like his description.
Jack and Kup did the Bears, unbearably, for over 20 years. The WGN studios at 2501 W. Bradley Place (an unforgettable address, since it was mentioned every day on Bozo) is said to be where the second fairway way. WGN moved in around 1960.
Mid-City was the first landfill course I know of. It was dug out for material for bricks, then filled back in. I don't know if the plan was to make it a golf course, but L&M came along either as the hole was filled or soon after.