As pointed out the ranking of best to worst really doesn't make sense here. There are a lot of issues that come into play. (Even if we ignore things like reliability and cost...).
The main reason is that it hugely depends on what options you have for the next stages.
If you have very good rocket technology (high TWR and ISP) then high mass to low speed is more helpful than low mass to high speed, compared with poorer tech.
This is because it takes exponentially more mass to change a rocket's velocity by a fixed amount. Another way to interpret that is it takes a fixed fraction of the mass to change velocity by a fixed amount. However what mass fraction is needed, for a given change in dV, is dependent on the rocket.
So the question "how much faster to you have to go to make it worth having half the mass?" doesn't have a natural answer. It depends on the final goal and what stages you have left.
Though in this case it's probably safe to say the Falcon 9 booster 'wins':
Falcon-9 block-5 gets 22,800 Kg to LEO and from 549,000 Kg at launch. About 4% which is pretty good. Stratolaunch's 250,000 Kg 'first stage' payload would not get as much to orbit using Falcon-9 tech scaled down as an actual Falcon-9.
There are also some other things that make this question really hard to give a meaningful answer to, for example:
The Saturn V famously 'oozed' off the pad, instead of blasting off. That because the TWR was very low when fully fueled. I this case gaining a small dV required a large theoretical dV. For the if there had been a first stage that had given it 100 m/s off the pad it would have gained around 400m/s in orbit if there was not atmosphere*.
In exactly the converse, the faster you are going in the lower atmosphere, the more losses you have. Hence extra velocity, while you are still in the atmosphere but with enough velocity to not be experiencing much by way of gravity losses, will not all be retained.
Putting your low ISP stages first:
Earlier on in the launch the craft is less susceptible to low ISP fuel sources (this is why rockets use SRBs as the first stage), so the rocket equations's constant mass ratio to velocity change doesn't hold in practice which makes it even harder to compare things.
[*] Imagine the TWR was 1.001 but somehow had 1000 time the dV, it would gain height and speed, but would be using almost all of the thrust to fight gravity with very little gain however once in space this is all gets used to add energy to the orbit.