GTA IV - The Ballad of Gay Tony

One of the more memorable quest givers from GTA IV was Brucie - an air-kickboxing, testosterone pumped, extreme-alpha male stereotype, he was always such an interesting rant on missions:

*  "Well I was nearly going to say as tight as my abs, but nothing is as tight as this, come on, you wanna feel?"
*  "I'm injecting bull shark testosterone, imported it from Siberia!"
*  "Brucie does not do five hundred crunches a day so he can cuddle f*cking cellulite!"

In Gay Tony, they introduce Mori - Brucie's older brother.  Having Brucie deal with his Napoleonic older brother - was - priceless.  He was reduced to a stuttering pitiable spineless klutz.  Brilliant.

The main character is a wise talking ex-street thug, and you have mission character stereotypes: 

• Tony: Flamboyant nightclub owner and you're partner.
• Rocco: Typical gangster.
• Mori: Brucie's Brother, hyper alpha male - wants to steal cars and race.
• Yusuf: The spoiled son of an Arab businessman, obsessed with stealing what he can't buy.
• Bulgarin: Insane Russian mobster.
• Your Homies: steal drugs from rival dealers.

I guess my biggest complaint would be that they really dialed-in the story, it really is just a series of missions with no purpose.  Tony borrows money from the wrong people, and you offer yourself as contract killer to his loan sharks.  Steal this.  Blow up these.  Kill those guys.  Walk into ambush.  Game over.

Still - this game is worth way more than the price of a pack of gum that they charge.