Your Monterey Club from Gardena, CA is worth about $10 according to Eastman, Rob. I'd say that's about right.

The River City, Crescent City Queen riverboat chip is from New Orleans about 1995. Your example has been cancelled by Paul-son and the overstamp has been removed by a collector. Worth about $5, IMO. Never cancelled versions are worth considerably more, but the high denominations are seldom seen. Watch out for chips that have the cancel impression machined off and resurfaced; there's a collector who is very good at this.

I'd agree that the Playboy is worth something in the $20-30 range. They are fairly easy to find.