As far as I know, Cadillac is unique among motorcar manufacturers in producing two very different V16 engines that were sold in production vehicles.
From 1930 through 1937, Cadillac made a 452 cubic inch, 45 degree OHV V16 engine with five main bearings for their senior models. During the entire eight year run, only 670 cars were sold.
From 1938 through 1940, Cadillac produced a 431 cubic inch, 135 degree L-head (flathead) V16 engine with nine main bearings, which was installed in a mere 514 cars.
Cadillac later admitted the company lost significant money on every V16 model they produced.
The link below goes to the Facebook page of "Freewheeling Tony Smith", who operates a gunsmithing and engine machine shop in Lewistown, MT. As the detailed build photos will show, Tony has the knowledge and the tools to rebuild and improve just about any automotive engine. According to his webpage, engines he built hold ten land speed records.
I'm not sure I even want to know what Tony billed the car's owner for this engine rebuild...
As an aside, for several years I stored a duplicate of the car pictured in the photos for a close friend in the basement of the duplex we rented in Chamblee, GA. For all I know, it may be the same car.