I want to play an "Uncle Buck" style rogue.

[underfoot007ct]

What is "Uncle Buck"?

"Buck: [is trying to make Tia go out bowling with him] We've done the battle of the wills. The deck's stacked in my favor. You're just gonna lose again.
Tia: Try me.
Buck: How would you like to spend the next several nights wondering if your crazy, out-of-work, bum uncle will shave your head while you sleep? See you in the car." ................................ Uncle Buck

 

[Rune]

But, what would this character do in a D&D Adventure?

Lets say the rules support this build 100%, would the adventures support this style of character.

In most D&D games (you know, the ones where the party includes someone who not only doesn't want to avoid fights, but is actually named after them) the focus would probably (usually) have to be more on evening the odds through this means, rather than keeping the fights from happening at all.

Obviously, this wouldn't work so well with unintelligent foes.

But, then again, Uncle Buck did show with the clown (thanks for the reminder, Minigiant!) that he can and will lay out some damage if the situation warrants it.

 

[Lord Zack]

Well the assumption that a dungeon-crawling campaign will consist of killing every monster you encounter is far from universal. It's possible that an "Uncle Buck" like character will prove able to con monsters out of their treasure or otherwise provide alternate ways of dealing with such obstacles.

 

[The Shadow]

He also arguably has Weapon Specialization: Power Drill.

 

[El Mahdi]

He also arguably has Weapon Specialization: Power Drill.

And Ranged Weapon Specialization: 1 Wood...with which he gets Sneak Attack damage.

 

[DonAdam]

It would be great to have a non-magical "expert" class to cover characters that lean on Int, Wis, and/or Cha but don't cast spells.