I have two responses for this thread.
The black car that a few thought was really ugly is a 1959 Buick Electra 225, the 4-door sedan (not the pillerless hardtop-sedan). The body style was used for two years, '59 & '60.
As for the black boat, it was made by AristoCraft in the 1960's. The model is the Funliner 17. It came as an outboard, with either this hardtop model, or an open cockpit. It's the little sister to the popular AristoCraft 19 with the sliding hardtop, the 19 being powered by an I/O. Both were great utility boats. I believe there are youtube videos of both boat models, and if you google "1959 Buick," you will find dozens of pictures of this big old boulevard cruiser; sedans, coupes, wagons, and convertibles. (My uncle had a silver '59 Buick Invicta convertible.).
AristoCraft 19 -
https://www.youtube.com/watch?v=E8JQPKrF69Q
AristoCraft 17 -
https://www.youtube.com/watch?v=t0388J27-qo
This boat is pictured on the webpage originally cited by the one posing the "Guess the boat" question.