In the US? Andrew '92 caused the most $$$ damage. The Great Galveston Hurricane of 1900 caused the most loss of life (8,000+ dead).

Andrew damage

Great Galveston Hurricane

Historically, there have been some other devastating hurricanes, both in terms of economic impact and also in terms of loss of human life. Mitch in 1998 caused over 11,000 deaths in Central America, the most since the late 1700's. Other horrific storms, from other parts of the globe include the 1970 Super Cyclone which struck Bangladesh, killing hundreds of thousands.

historic hurricanes

Bangladesh Cyclones

Camille 1969 was also particularly brutal, being a CAT V at landfall, although it was neither the deadliest nor costliest in the US.

camille

Hurricane Hugo in 1989 was also one of the harshest storms in recent memory. It was both huge and carried it's destructive rage inland for over 100 miles.

Hugo 1
Hugo 2

NOAA as well as NHC both have extensive information on "Killer Canes". You can literally spend hours there.

Hope you enjoyed the info.

PS. If you think it might be "fun" to be in one of these monsters, think again. There are a few folks on this board who've been through, I think, some Cat III's, but most will be evacuating early. And, if you are told to evacuate, GET THE HELL OUT!