You've got to cover a huge range. Elton and Billy are fine for 70's, 80's, and some 90's, but cruise ships are also full of older folks who want the Frank Sinatra and Paul Anka from the 50's and 60's. Throw in some Nat King Cole, Tom Jones, Englebert Humperdink. Harry Connick, Jr. and Michael Buble have both recorded albums of standards; check out the ones they've covered, because there's a reason those songs were picked.
Search online for the Billboard Top 100 songs for every year since 1950. Mark every song that's done by a solo singer as opposed to a band or instrumental (and that's going to start off being most of them, but the ratio will shift over time) and learn at least half of them, more like 3/4 of them, minimum. If you're gonna sit down at a piano and be the guy that takes requests and knows any song someone requests, you gotta actually know all the songs, or at least know the vast majority of them. If there's one that you don't know, people will forgive you, but if you ever hit a string of two or three requests in a row and don't know, don't know, don't know, people will think you suck (and they might be right).
I thought at one time that I'd like to do exactly what you're talking about, then I realized how many hundreds, actually thousands of songs I'd have to learn.