Artists who arguably have produced BOTH the best AND the worst in their field

There may be a bit of that. I’d have to rewatch it – I only saw it once c. 2001/2002. But I do remember his quirks fitting the character perfectly and driving the story perfectly. As you say, it may have a bit to do with the his antics being perceived in a more realistic manner, but whatever the case may be, I felt he was perfect for the role. I also recall his character being reined in a bit – quirky but not as over-the-top as usual – quirky Adam Sandler, but within the bounds of what I perceived as realistic.

ETA: Holy crap–did it really come out as late as October 2002? Damn, that doesn’t gibe with my personal chronology, but, hey, there’s no arguing with facts. So I would have seen it probably in 2003, as I rented it on VHS while living in Europe, and I moved back to the US in Nov 2003. Damn, memory is weird.

For me, a tedious achilles heel of theirs was “The Golden Age of Ballooning”.

Bearing in mind, though, that a b-side was quite often not “strong” or “popular”. (please note quotes) Often it’s an obscure confection, like “You Know My Name (Look Up the Number)” as a b-side to the Beatles’ “Let it Be”.

Nat King Cole was an absolute gift in his time, but stunk the place up with his last two chart hits, "Ramblin Rose’ and “Crazy Days of Summer”.

For me, the blancmange sketch is the nadir of MP.

Not quite “best and worst” but Jimmy Webb is responsible for both the sublime WICHITA LINEMAN and the horrendous MACARTHUR(S) PARK.

Sure, that’s common, but my example has the worst (strong and popular) on the a-side and the best (obscure madness) on the flip.

Nat earned an awful lot less as a superb jazz pianist than he did as a pop crooner, and I’d hardly call your examples the “worst in their field”. Jim Nabors easily beats him.

Another Clapton moment. At the 2007 Crossroads Festival, he totally stepped all over Steve Winwood’s singing. More than a few times Winwood has a WTF face and stopped singing. Yes, I know it’s Clapton’s song, but it was Winwood’s singing on it during *Blind Faith *that made it a classic.

Think of Dylan like a gold mine. There are a lot of gold nuggets there, but they’re mixed with a lot of ore. Even his ore is better than a lot of artists’ best stuff. His gold- unbeatable.

How about Johnny Depp? A lot of great roles then… Tonto.

Would like to note that a lot of Mozart’s early work is so bad it sounds like a child wrote it.

And Oscar was worse than all of them. Seriously, who said “You know what the world needs? An old-tyme farce starring Sylvester Stallone, that’s what!”?

And the person who apparently said this was John Landis who directed it, and thus also earns himself a place in this thread. Actually, Landis earns it for the two Blues Brothers films, which were respectively brilliant and horrific.

This explains his recent effort The Ridiculous Six which is horrible even by “bad Adam Sandler film” standards. It only makes sense if you understand it as Sandler rounding up some friends to make a stupid Western he’d written. It ought to be offensive to Mexicans and Native Americans, given the grotesque caricatures of both in the film, but it’s so bad I suspect both groups would avoid complaining just to avoid any association with it at all. I beg you - don’t ever watch it, for your own sake.

ISWYDT.

Forget to mention re: the Beatles - I’d put Why Don’t We Do It In The Road at the bottom of their oeuvre. I mean yes, the title’s funny, but it just sounds like McCartney got drunk and busked this one.