Best and worst are subjective of course, which makes this game a little easier. Which artists – any medium – could be argued to have produced both the best work, and the worst work in their field.
Here are a couple to consider:
Laurence Sterne – this is slightly unfair. Tristram Shandy is a towering work of genius. I might even argue that this work, written in the mid 18th century, more or less exhausted the possibilities of what could be achieved with the novel. And Journal To Eliza is maudlin, mawkish, lovesick crap. And those are its good points – but then it was never intended to be published. So, as I said, slightly unfair.
Johnny Cash, though – no excuses. There is so much to admire, but I’ll keep it to a couple – from the early years there’s I Walk The Line; and from very near to the end, when he was close to death, there’s In My Life. They are so well known that there is no need for me to heap praise on them – the links are there just for you to enjoy. And then there’s A Boy Named Sue. Speechless. Well, not quite – that’s the thing with country, it’s done on a cliff-edge of sentiment and emotion, and when you take it that little bit too far, you fall off the cliff. No link for this one. It would be inhumane.
Phil Collins. He took part in writing some of the best music of all time with early Genesis. Then he later embarked on a solo career.
Jon Anderson, Steve Howe, Rick Wakeman: Some of their solo stuff is the most insipid crap ever made. After listening to it, it’s hard to believe these are the same people who created Close to the Edge.
Cash may have sung “A Boy Named Sue,” but it was written by Shel Silverstein, and is right in his wheelhouse (e.g., “The Unicorn,” “Sylvia’s Mother” (and most of Dr. Hook’s earlier work), and The Giving Tree).
Alfred Bester wrote to classics of the SF field, The Demolished Man and The Stars My Destination (both of which hold up pretty well today), then returned to novel writing with The Computer Connection (good start, but falls apart halfway through) and Golem 100. His reputation dropped precipitously after that.
For science fiction, my pick would have been Heinlein. On the one end, The Moon is a Harsh Mistress is a serious contender for best SF novel ever written, and plenty of his other works are likewise excellent… and then you have drek like Number of the Beast.
Even if you restrict it very narrowly, say, to time-travel short stories, you’ve got “By His Own Bootstraps” and “All You Zombies”, compared to “Elsewhen”.
I thought this thread was going to be about Adam Sandler. OK he isn’t be accused of making the best movie of all time but Uncut Gems is being widely acclaimed with award show buzz. And then there is Jack and Jill
But thinking of Jack and Jill there may be a candidate. It can be argued that Al Pacino has given the best acting performance in The Godfather. I won’t argue with you if you say he gave the worst performance ever in Jack and Jill.
I’ll go with Adam Sandler. Happy Gilmore is going to be in the list of the greatest comedy movies of all time. Then anything made in the last 20 years is going to be near the bottom.
John Wayne: there was The Shootist, and then there was Riders of Destiny, wherein he played a singing cowboy. Granted, he was only 26 when he did the latter.
McCartney was one of the first names I thought of, but I’m not sure it’s fair to mention people like him. True, there’s a huge gap in quality between his best stuff and his worst stuff. But is his worst stuff really at the bottom of all the millions of pop and/or rock songs ever recorded?
The thread title question may only be answerable if we don’t take “worst in their field” too literally.
Shakespeare wrote both Hamlet and Titus Andronicus. While the latter is far far below his best, it probably doesn’t qualify as the worst play of all time.
Will Eisner created The Spirit, the masterpiece of expressive comic-book art that winks at a bare minimum of ‘superhero’ basics to instead do ‘private eye in the big city pairs detective work with the ability to take a punch while investigating crime after crime and crossing paths with femme fatale after femme fatale’ storytelling that transcends the genre.
Ebony has issues (mostly his appearance), but there are a lot of positive aspects – the Spirit accepted him as an equal and Eisner never used him for racial humor (other scripters who took over when Eisner was in the army did lapse).
Stephen King: Went from the top of his game with 'Salem’s Lot, The Shining, etc. to Tommyknockers, which was pretty dreadful. Probably not the worst horror fiction ever written, but a good demonstration of why you shouldn’t do drugs.
Stevie Wonder’s early Motown stuff was already astounding, but the 5 albums from “Music Of My Mind” from 1972 to “Songs In The Key Of Life” from 1976 are transcendental. Well, later he made “I Just Called To Say I Love You” and “Ebony And Ivory”, two of the most trite and banal pieces of music ever put on a record.
Philip K. Dick is my favorite author, and he wrote some truly great novels like Ubik and The Man in the High Castle. However, to pay the rent he cranked out some lousy stuff, like Vulcan’s Hammer.
Beethoven wrote an orchestral piece called Wellington’s Victory which is a wacky, noisy mess, but it gets played once in a while because it’s got Beethoven’s name on it.
Neither of these examples are “worst in their field,” but if all of PKD’s and Beethoven’s works had been at that level, both of those guys would be forgotten today.