Static and Dynamic Displacement and HP

I'm not talking any particular displacement or rpm. Could 170 vs 225, 318 vs 360,
340 vs 360, 440 vs 500, 500 vs 543 could even be 289 vs 340, 273 vs 396 etc.. To narrow it down could say 360 vs 408 with same or similar top will the 408 always make more hp from say peak torque to peak hp ? And if so why can't the 360 spin up and extract the same hp out of the top end ?
I started off on the wrong foot here. Rat Bastid helped me out a bit. I think usually the 408 will make more power overall but I tend to believe the 360 may make more per cube. My 367 made around 1.6hp/CI I believe I would see more power with that top end on a 408 but I think the heads would be a limiting factor and it may not make the 1.6 or higher mark due to rpm limitations. All just guessing with limited experience here though. Are we starting with heads set up for a 360" or 408"?