I'm not going to comment on the political correctness - or lack thereof - of your request. Instead, I'll suggest some song possibilities.
For baritone:
"Some enchanted evening" and "This nearly was mine" from SOUTH PACIFIC. The character of Emile Lebeque was ostensibly Francophone, but the role was created by Italian bass Ezio Pinza, so accent would certainly be acceptable.
"Dulcinea" and "Impossible Dream" from MAN OF LA MANCHA. As Placido Domingo proved on the Sony studio album, it's a role that can certainly be sung with the appropriate accent (given the character's nationality).
"Joey, Joey, Joey" from THE MOST HAPPY FELLA. The character is actually Italian, but I suspect your friend could get away with singing it with an Italian accent.
"Only with You" from NINE. The character of Guido, based on Federico Fellini, was created on Broadway by Raul Julia.
For Tenor:
"High flying adored" from EVITA (you already mentioned the role of Che; this is one of his more engaging songs, IMO).
"Giannina mia" from Friml's THE FIREFLY (operetta). Sung by a Frenchman posing as a Spaniard, who happens to be singing an Italian love song in English. Go figure. "The Donkey Serenade" from the same operetta might be an even better choice.
"To each his Dulcinea" from MAN OF LA MANCHA
Perhaps there's something from Cole Porter's MEXICAN HAYRIDE...
Karen Mercedes http://www.radix.net/~dalila/index.html *************************************** What lies behind us, and what lies before us are tiny matters compared to what lies within us. - Ralph Waldo Emerson
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