Question:
I agree with Gimpy and Mr. Ben:
Bvlgari pour homme
AND
Bvlgari pour homme Extreme.
Check this out:
FS376 Bvlgari by Bvlgari TESTER for Men Eau de Toilette Spray 3.4 oz $70.00 $22.95-------> that is crazy cheap. I can vouch for the quality too! Sorry this is from Fragranceshop.com. I should note that the TESTER is 100 percent full and never been used. The box is just non-descript and the cap might be missing. Other than that, same as one New In Box (NIB) with shrinkwrap.
LAST edit: the $70 indicates what you pay at Niemen Marcus. the 23 is FS. OK, I'm done. (I love Fragranceshop)

Answer:
Originally Posted by Dante Gurlain Heritage. Yes, Heritage. An all-time woody spicy fave. My SOTE. I actaully prefer Heritage to Creed's Bois du Portugal.
Also test Quorum, Michael Kors Men, and maybe Versace Dreamer for a tobacco note.

Answer:
There's been some great recommendations so far (as always)! I'll second Terre d'Hermes and Dunhill Edition.
Burberry London for Men - tobacco, port wine, spices and leather. Very sophisticated and modern.
Guerlain Vetiver - vetiver and tobacco. Not like D & G, but a classic and great for Summer!
Aramis Havana - The king of tobacco scents! Woods, spices and tobacco. A classic.
Boucheron Jaipur - no tobacco but sophistication galore!
You should be able to buy several of these and still stay under $100.

Answer:
Guerlain Heritage
Chanel Antaeus

Answer:
Kiton Men
Heritage
Chevalier D'Orsay
G-11 by Il Profumo (at luckyscent)

Answer:
Not sure what sophisticated is to you, but for your price range:
Geir
Gendarme
Acqua di Parma
CdG 2 Man
Paco Rabanne Pour Homme
Richard James Savile Row
TNMA

Answer:
Tobacco scents:
Tsar, by Van Cleef & Arpels
The Dreamer, by Versace (I don't like this one)
Creed Tabarome Millesime (under $100 at places like scentiments.com)
Creed Vintage Tabarome (buy a decant)
Havana, by Aramis (discontinued in the U.S., but still around if you look hard enough)
Here are my favorites in the sophisticated category:
Patou Pour Homme [discontinued, and expensive, but our own Azsmells has it to sell]
New York, by Parfums de Nicolai
Creed Bois du Portugal
Chanel Pour Monsieur (1955)
Chanel Pour Monsieur Concentree
Caron Third Man

Answer:
Give Dunhill Homme (2003) a try. You can find it for about $35 online and it is the best bang - for - the - buck cologne I own and a personal favorite. It should be right up your alley not only with price, but smell as well!

Answer:
Piece of cake!
Guerlain Heritage
Chanel Antaeus
CD Eau Sauvage
Escada Pour Homme

Answer:
If you are shoping at Sears, you might be a little limited. I would think Aramis 900 would be very sophisticated and very available.