Reality and perception clash in the everyday activities of a Hollywood Legend. Getting your own Grande Skim Macchiato should be easy enough, but for this Diva, an unexpected encounter leads to scandalous results.
Tom ties up Spike and sneaks into the courtyard of the glamorous Toodles Galore with his bass, hoping to woo her with his song, much to the annoyance of a sleeping Jerry.
Goofy, staying at the Sugar Bowl resort, demonstrates the basics of downhill skiing, which the titles and announcer insist is pronounced "SHEEing". The equipment is, of course, of the era. As you can imagine, Goofy has much trouble keeping his skis parallel and pointing downhill. The final ski jump conveniently lands Goofy right back in bed.
Tom heads for a big city penthouse to become acquainted with a rich pretty female cat that lives there. He brings her Jerry as a gift and does some humiliating things to Jerry. Jerry, in turn, attracts the attention of another cat who also becomes interested in the female cat. It eventually turns into a fight between Tom and the other cat for the lady's hand but Jerry is the one who gets her in the end.
Chip and Dale are starving in their tree home when they notice a plentiful supply of acorns on an island in a lake. To get to the island, they borrow a miniature model ship of Donald's to sail on. The irate Donald, however, doesn't appreciate them stealing his ship and makes several attempts to get it back and thwart their scheme to get to their acorn paradise. Chip and Dale are, of course, always one step ahead of Donald.