If she's a heifer, go with something that is well known for calving ease. The last thing you want to do is take a chance and mess up a good heifer. I've never used either, so someone else may be able to answer this better, but I don't think that Cherry Bomb is "calving ease". RE Johnny Walker Red, I've always kind of liked his looks & I think he had a fairly light birth weight. I may be wrong, but I also don't really think that JWR would be classified as "calving ease", although I think he would be more so than Cherry Bomb.
If it were me, I'd probably consider Jake's Proud Jazz. He is built pretty nice & has a nice looking phenotype. He's also known to have a little calving ease. Since he's a Shorthorn, you could register the calf as a Durham Red / Shorthorn Plus.
I don't know about the hair part (I think that he would have some hair), but the Shorthorn bull, American Muscle, should certainly stouten her up & he's calving ease from what I understand. I think he's a Gizmo decendant & IMHO, Gizmo is a pretty good bull. American Muscle doesn't have a "freaky look", but if you closely study him, he's put together pretty well & if you are wanting a show steer or a heifer to keep, American Muscle could be a good candidate.
I'm sure that I've missed a ton of bulls, including Red Lowline bulls, but for what you are wanting to do & describe, Jake's Proud Jazz sounds like a good mating for her & I wouldn't be scared of trying American Muscle.
On calf #2, you may want to try something a little more "Clubby", but for #1, stay with something known for "calving ease".