One thing that monopoly has in its favour is its language is extremely familiar. You have money (like real money, not stupid cardboard disks) and things like buy and sell. This must help a lot.
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The game that has been the most successful with non-gaming friends for me is hands down Codenames - I think because it feels similar to games non-gamers know (an abstract word game like Scrabble ), is very simple to understand, and is fun straight out of the gate.
There are many games I’d rather play, but I can’t deny I’ve had lots of fun with this with non-gamers and it’ll never be unwelcome for me for that reason. I’m pretty sure it’s not inspired many people to be gamers but it’s inspired a lot of sales of the game with people I’ve tried. I’m not sure if it’s like anything but better but I’d certainly recommend it as a change from Scrabble, Pictionary, Trivial Pursuits or similar favourites. It certainly doesn’t outstay its welcome, it’s genuinely fun, compact and fairly cheap.
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I think you can get the idea of what you are dealing with using Splendor as a rulestick. With my partner, this and Welcome to is how deep she wants to go. Which is fine. Considered an entry point game by us in the hobby, one of my friends played it once when we were in the beach for a weekend, and claimed: “Nice game, but I don’t like games this long.”
So that gives me the reference, with her, nice and simple does the trick. Which, again, is fine.
I must say, I do not agree with the fact that you cannot have a good time with Risk. Or Monopoly. The problem with them is that they are designed in such a way that only one person has a good time, and everybody else struggles. Or hates it. This leads to banter. Or hatred.
I must say, we have available plenty of games that could be a good hit with the big masses. To a degree, Catan, Pandemic and Ticket to Ride have been, and now Wingspan is jumping on that hype wagon too. But there are plenty of part games out there that could really become classics given the right frame. The main problem, as @pillbox mentioned, is that non-hobby-gamers, or casual gamers, don’t tend to want to learn rules, or complex games. And that is the threshold to beat.
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I wish I had something a little more eloquent to add to this post, but hopefully this is still worth saying—I caught myself thinking about what you wrote well after reading, so there’s more thought into this than the next few words might indicate.
I think many hobby gamers could be reminded of that bewildered outlook about gaming. Experience lets us chase mechanisms and concepts that have worked in the past but with how often so many of us—myself included—bemoan the flops and churn out duds (many of which are highly rated), I think it speaks to the importance of understanding the essential experience you want at your table.
Hell, there are more than a few conversations right here discussing the shift in tone at SUSD (and why Tom has been increasingly fun to watch), the gang that unified most of us (at least on this channel) and who always went out of their way to try and evoke the “table feels” in their coverage.
I guess I said more than I expected, but just the same, good post. Got my noodle boiling. 
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