Can anybody help me????

So I'm driving myself crazy trying to find this movie I watched a few years ago. In the movie a guy owes a man money. He's in a lot of debt and so the man he owes money to sends a hit man type guy to kill him. I think but might be wrong that the two guys know each other. The two drive around and the man who is in debt is trying up lose ends and taking care of things while the the hit man accompanies him. At the end of the movie there's a scene where I think he's about to be killed by him but I'm not sure if he does it. The movie is a dry comedy so it's not an action movie or anything. It was a good movie but don't think it made it to movies. I cant for the life of me remember any of the people in it but I'm pretty sure one of the leads was pretty familiar