No, if he wants to raise a serial killer, he can stick with Lester, but make sure the kid’s middle name is Wayne.
You all know that Lester Wayne Mudd is just a headline waiting to happen.
But he’ll be all set for his career in soap operas.
Add me to the chorus of “No’s.”
As someone else said, I first thought “Lester the Molester” and then thought “Les Nessman.”
Yeah…my first thought when I saw the OP is that I hope if his real last name is Mudd, his daughter doesn’t run into any old-style Star Trek fans. My very first thought was of Harry Mudd and his wife Stella: “HAAAARRRRCOURT! Harcourt Fenton Mudd!”
Another vote against Lester. My first association with that name is a ventriloquist dummy (anyone remember Willie Tyler and Lester?)
Sterling and Stella go together well (I adore the name Stella) and are both ‘star’ names.
I actually don’t think Lester is that crazy of a name, it’s just old-fashioned at the moment and has some negative/humorous associations for a lot of people. But I agree with PPs that being widely known as ‘the Molester’ and ‘Lezzie the Lesbian’ would probably be in the future for your little Les. If you know such bad nicknames are such a certain part of your kid’s future, I think it’s wrong to go ahead and give him a difficult name.
Ha! I had forgotten that his wife was named Stella. (The person dubbed me “Mudd” 20+ years ago was a bona fide Star Trek geek; no coincidence there.) I think I may need to get her some little Stella Mudd kit, now. (Her mom already uses our names interchangeably, to hysterical effect. Maybe it’ll be simpler if we can both be “Mudd.”)
“Sterling” is starting to grow on me, but I’m still going to cling to “Lester” as a useful foil against daycare expenses that we can’t possibly budget for within the next year or so.
How about Lestat, the tough vampire version of Lester. All the kids love the vampires these days.
Listerine Mudd. 
Clay Mudd
Lestat? That simpering little emo bitch?
Yoname Seymour Mudd
(Yoname S. Mudd)
Go for twins: Lester and Hester. Or Lester and Fester. They’ll be so mad at you over the names they’ll never have time to fight with each other.
Let’s not forget Chester. And Nestor.
“If you want to torment him you could call him Cecil.” - John Candy in She’s Having A Baby
This evening I asked a group consisting of my teen daughters and two of their friends (4 different ethnicities) what they thought of the name Lester for a guy. They all burst out laughing.
You can’t name an American kid Alaister or anything like that, he’ll be known as “Alice”. Jeez.
Lester = Fester. Festering wound. Yeah, that’ll attract girls.
Lester Wiggins?? (Seriously? :() That unfortunate name does not resonate with success in any capacity. The poor thing. Sounds like he lives with his mother and they walk to church every week, and he wears a white short sleeve shirt and a red bow tie and he carries their bibles.
Orion**.**
i can’t believe this has 2 pages and no one named the most famous star name.
lucifer
much more macho than lester. lucifer eats humans named lester before the morning star shines.
salinqmind, he strongly resembled a young-ish Barry Manilow, but I have no idea how popular he was/wasn’t with the ladies. I don’t know what his parents were thinking when they named him, though.
So your first child is named (essentially) “Star”, and now you want to name your second child (essentially) “Less Star”…?
Who could have a problem with that, other than the kid whose life you’re screwing up from the get go?
I make this argument every time I post to a thread about kid names. Still, I’m another vote against Lester. It’s just a bad idea and at least as far as I’m concerned it’s an ugly name.
I think I like it. The assonance thing is a little cutesy, but it fits the OP’s criteria and they do go well together.
Old fashioned names are pretty popular in some circles. Not all old-fashioned names are good. 
There’s nothing wrong with the names themselves, but if you look around the SDMB, every time someone solicits baby name ideas you’ll see someone shoot down a creative suggestion with a comment like ‘I don’t understand why people think of names like this when there are so many good dignified names with history like William and Arthur and Henry and…’ the list goes on. There’s nothing wrong with doing something different and avoiding both the grandpa names and the “new” names like Hayden and Cayden and Wayden. But I’d still stay the hell away from Lester.