Minor league hockey has done a great job of "having fun with it, but not getting too crazy."
Minor league baseball had a period like that, with the Isotopes (after the Simpsons episode), the Montgomery Biscuits, Lansing Lugnuts, Modesto Nuts, Akron Rubber Ducks, Rocket City Trash Pandas and Richmond Flying Squirrels. They fit their city/region, had a playful logo, drew attention to themselves in a positive way and staying as a really awesome name/merch revenue driver.
... but minor league baseball just went full tilt, where the main goal was the PR from announcing your name change and first month of merch sales. Then the fans are stuck with a ridiculous name: The New Orleans Babycakes, Hartford Yard Goats, Binghamton Rumble Ponies, Jacksonville Jumbo Shrimp, Amarillo Sod Poodles.
(To be fair to New Orleans, the writing was on the wall that they were gonna have to move, so they decided to change the name in the last two years for a merch blitz tied to the city before they bounced).