Question:
I was thinking about how to introduce a friend to fragrance. I figure the first thing is to establish what classes they prefer, as in Oriental, Floral, Citrus, Fougere, Leather, etc etc. To figure this out, you would go into your wardrobe and select a representative fragrance for each class.
So the question is: what would be the categories you would choose, and what would be the fragrance in your wardrobe you would choose as the most representative of each category?
Off the top of my head, I'd say:
Floral for men - Chanel Pour Monsieur (original, non-concentree)
Leather for men - Aramis or possible Jean Pascal
Citrus for men - Eau Sauvage
Oriental for men - Obsession
not sure what I would pick for Fougere...
What do you think?

Answer:
Old-time (perhaps a bit dated) classic fougères:
Caron pour un homme (1934)
Monsieur Rochas (1969)
Classic (in a more timeless way) fougères:
Paco Rabanne (1973)
Azzaro (1978)
Modern fougères:
Drakkar Noir (1982)
Herrera (1991)
You mentioned Chanel Pour Monsieur as representative for florals, and Eau Sauvage as a representative for citrus. For me, it's the opposite: Pour Monsieur more like a citrus, and a heavy floral/jasmine character for Eau Sauvage.
I would not necessairily select the best frags to accomplish your intent, but those that would best teach him to recognize each categorie, in a beginner's level.
So:
Citrus Chypre: Armani
Fougère: Drakkar Noir
Leather Chypre: Quorum
Oriental: Obsession
To expand his learning:
Citrus Chypre: Boucheron
Fougère: Herrera
Leather Chypre: Trussardi
Oriental: Egoiste
I would not set florals as a scent family for men, even if some frags have characteristic floral notes (like Eau Sauvage, Van Cleef & Arpels and Dior Homme).
Peace