And with weathered wood...

I like the weathered wood. The black seems too heavy and makes the black brick stand out too much.

Our roof blew away in a storm and was replaced a few weeks ago. I was not sure what color I wanted to replace it. My contractor had a list of addresses of houses his company worked on and each of the houses was identified by roof color. I drove around with my maps and this list so I could see how the roofs looked in real life. The way the roofs look on a tiny sample is totally different than how they look up on the house. I would not pick a roof from a tiny sample. In the end, the color I thought was too dark was a charcoal black. It looked terrible on the sample but looked good on people's houses and it looks great on mine. Also, if you can't do that maybe you can drive around your town and find houses like yours then make note of their roofs and find a color that comes close. I have a brick house with the same kinds of colors as yours. We have dark green shutters and a dark green front door and white trim. The black looks perfect.

Also, people on here can be more help if you post a picture of your whole house. Then they can see the style, the trim colors, etc. It might help.

Good luck! It is a big decision and expensive so you want to get it right.

Yes, seeing a wide expanse of shingles is very different from seeing a sample. My roofer did the same as Judithn's -- gave me the addresses of other houses they had done and the name of the shingle they used. It was extremely helpful. It also helps to look at it at different times of day if you have time. I went with Certainteed Colonial Slate shingles on my brick house. I'd have to say that it is about half way between your samples. The Certainteed web site has a wonderful feature where you can see how their different shingles look on different houses. You can download a picture of your own house and "try on" different shingles.