I'd say there's too many preferences for us to agree on 5 specific models.
I offer:
1. 1911, They're incredibly ergonomic (to most people with small hands to giant paws). Nice and soft shooting, plenty of punch, and atypically better than average trigger.
2. Glock, pretty much any of them outside the baby Glocks. I find they all shoot pretty similarly. You gotta see what the fuss is about, whether or not you choose to drink the tacti-koolaide is up to you.
3. 4" 38/357 Med. frame DA/SA revolver preferably with adj. sights. S&W 10,64,15,19,66,686 Ruger GP100/six series, Dan Wesson et. al. These are almost just as inherently American as a 1911 and some of my favorite guns to shoot.
4. .22LR pistol 4-6" barrel. Either a S&W K22, or a Ruger or Browning. Theres lots of fun to be had for anyone.
5. Something that starts with "4" and ends with "agnum" or comparable. What can I say? they're a blast (pun intended), and they're a shooting discipline in and of themselves.