Which actors or actresses have had career arcs that just plain surprised you?
Bruce Willis - from “Moonlighting” on TV to big-time movie star, in everything from classic action flicks to “Moonrise Kingdom”. surprised me.
Matt Damon - mild mannered guy roles to ultimate fighting machine in Bourne movies. also surprised me.
Elijah Wood - from child star to Frodo to starring in Wilfred with a guy in a dog suit.
Ed Norton’s performance in American History X definitely surprised me.
Ryan Gosling -from Mouseketeer to Lover Boy to Indie Darling to Badass Hunk.
Bryan Cranston - from sitcoms (Seinfeld, Malcolm in the Middle) straight to serious drama (Breaking Bad).
Before that, Cranston was a voice actor. I remember being surprised to find out that he’d done the English dubbing of The Wings of Honneamise, which was back in 1995. (Surprised, because the English dub fell flat and yet Cranston appears to be a great actor, now.)
I wouldn’t have pegged Shakespearean veteran and supporting actor on I, Claudius Patrick Stewart to become a starship captain on a sci-fi series, let alone a cartoon voice actor playing such an obvious parody of himself on Family Guy.
I always thought the arc of Freddie Prinze Jr. and Chris Evans was pretty weird. In 2001 Prinze was a leading man and Evans biggest role was playing a parody of Prinze. Now Evans is freaking Captain America and Freddie hasn’t done anything big since 2004.
How about Hugh Jackman - From singing and dancing as Curly in Oklahoma! to Action star as Wolverine in the various X-men movies.
Probably Evel Knievel jumping the Snake River Canyon. Oh.
DiCaprio. Forgettable sitcom kid. Promising youngster. Tiger Beat Fodder. Serious actor for Scorsese, Nolan, Tarantino.
Although the Borne movies were pretty good, I still don’t buy Matt Damon as an action star. Scrappy little Irish guy, sure… secret agent strong enough to kill people with magazines… dont think so.
Ian Gillan–fronted Deep Purple, sang the part of Jesus in the original recording of Jesus Christ Superstar, fronted Black Sabbath, did other stuff, returned to Deep Purple.
Leslie Nielsen. Up until Airplane, his roles were mainly dramatic. After that, he was known for comedy.
I can’t remember what magazine I read it in, but Sarah Michelle Gellar gave an interview recently where this question came up and she actually replied with some variation of “He’s been doing me since 2004.”
New respect for SMG!
When Melissa Gilbert was married to Bruce Boxleitner, an interviewer mentioned the title ‘What’s Eating Gilbert Grape?’ and then asked ‘What’s eating Gilbert?’- Her reply- ‘Boxleitner!’
My first thought to the OP- Peter ‘Bad Taste/Meet the Feebles/BrainDead to LOTR/The Lovely Bones/King Kong’ Jackson.
Christopher Lee: WWII British OSS agent to Movie Actor to Elderly Metal God.
Marky Mark Wahlberg. From a life of juvenile crime (including taking some guys eye out) - to rapper - to underwear model - to a very busy actor. What are the odds???
In his case, a constant level of personal assholery seems to have been maintained throughout.
I know, that’s the thing! 
AND a succesful TV show producer with a show loosely based on him.
He also popped up as a guest star on How I Met Your Mother in season 1 or 2 (I started watching the show for the first time from the beginning a couple months ago). Also making an appearance was Bob Odenkirk (“Call Saul!”) Seeing both was a delicious treat, as a Breaking Bad super-fan/geek.
My entree: Speaking of Leonardo DiCaprio … no thread of this nature is complete without the mention of Bosom Buddy Tom Hanks.
Shatner was a Shakespearean actor. As was Avery Brooks.