The field used to be a bit more varied when it cae to football video games. These days, it seems like Madden is the only thing anybody plays. NFL Blitz is another series of football games that was first introduced as an arcade game in 1997. It was also ported to a few home platforms, including the Nintendo 64, the following year.
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NFL Blitz (Nintendo 64)
The second photo features a boat called the Greyhound II. I found references to a charter fishing boat in Key West with that name that was operating in the 1950s. The best photo of it online I have found is here: https://www.keysnews.com/community/today-in-keys-history/article_5a8a1114-28c3-11ef-9497-9f392e88e30a.html - it does look like the same boat.
Vintage Photos - Lot 3 (237-240)
Emerald Rose performs Take Me Down (to Her Water) at MegaCon 2012.
MegaCon 2012: Emerald Rose (7) - Take Me Down (to Her Water)