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used to ride a single chainring on the road...it used to come off quite regularly when cross-chaining.
Technically, you can't cross-chain on a single ring. Cross-chaining by definition means the chain centreline crosses the centreline between the outermost and innermost chainrings, a mathematical impossibility in the case of a single chainring.
I've found that unless you're doing big shreddz, a NW ring has much more of an impact on chain retention than a clutched mech, and generally a 1x drivetrain happily runs with just the NW ring.
For mad sendz & that, you'll want a clutch.