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First Louie states: "10 CLUES IN A ROW WITH SOLID CONNECTIONS" Then uses this as an example: 152. California Coal Miner's Attire -- Neil Diamond Greatest Hits Vol. 2 -- I'm guessing the "Forever in Blue Jeans" track. That sure doesn't seem so solid t...

"Well the Alaska one was because during the gold rush, potatoes were almost as valuable as gold!" Not even close :^O

Yukon Gold is a potato, but the Yukon is a Canadian province, not Alaska. Another vague clue

The Californian gold rush actually started in the area known today as Sacramento.

cotton = cotton gin, cotton picking, cotton shirt, cotton wads, cottontail rabbit, cottonseed oil and so on and so forth. Winning is a matter of chance.