I just finished reading this great book on cartoonist Virgil Partch, who defined cartoon weirdness for several decades.
The book revealed that Partch was a great joker in real life as well. He and some buddies founded the Balboa Island Sculling and Punting Society, which was an excuse to putter around the marina, freak out the squares and get drunk. Not satisfied with those activities however, they aimed higher. First they decided to take a "boat ride" from their West Coast hangout to Las Vegas. How? By putting a boat on a truck and riding inside the craft while being driven across the desert.
Then they decided to take a train to Catalina Island, by a similar expedient.