But that saying, authored by Milton in Paradise Lost, is ascribed to Lucifer/Satan. Not exactly a fountain of wisdom and good judgement.
Also, Milton wasn't particularly orthodox, but in conventional Christian theology Satan is not said to rule in Hell- he suffers with the rest of us.
In an absolute sense, though, it would only be better to rule in Hell than to serve in Heaven if the status of a servant in Heaven was worse than that of a ruler in Hell. Status is relative, but not only relative to the other participants in the study - it's relative to the entire population. I'd prefer to get $10 and have one neighbor get $20 than $8 and $5, because the wealth of millions of people establish the price of goods to me, not one person getting a little more. In a world where a million people get $0, I get $10, and someone else gets $20, I'm relatively wealthier than if a million people still got $0, I got $8, and my neighbor got $5.
Yeah, it might be more economically rational to seek to get $8 million if the entire world was going to get $20 million if I didn't take the option, but then there's the old saying "a rising tide lifts all boats..."