I am conflicted. I think the Jack is a prettier chip but because it has the same edge spot pattern as the Red Rock $5, I see a reason to use the Hollywood.
I actually like the Jack $100 better because of the spot progression (it's not the same as the $5), but I'm not a fan of the label. Assuming you are relabeling, definitely got with B. If you are not relabeling, A. is acceptable.
Also, looks like you have a frac, which makes me believe the $100s won't get on the table often. If that's the case, there is no wrong answer.
Also, hat tip on the use of the Wheeling Island $1s. I love that chip.
Funny how these things happen. I actually fell in love with the Stardust $1 chip with the tan edge spots and decided to create a set around that. Unfortunately, availability and cost made that difficult. That is how I ended up using the Wheeling Island chip that I am also fond of. I came up with 2-3 of each denomination to potentially use but found their inlays impacted how they looked so I stuck majestic stickers on all of them to see what they would look like in a cohesive set. That is when I realized how the Red Rock $5's just pulled everything together.
See what I mean?
Much closer with the matching labels on top. And I do agree with Wedgerock, if it rarely hits the table then go with the best/prettiest one. I think the B is a better stand alone chip