It's been a recent fad for Hollywood actors to publicly declare that they're going to retire: Shia LaBeouf, Alec Baldwin, Brad Pitt, and Jessica Lange have all made such threats in recent years. But to actually engineer a proper last film? Well, it's harder than it looks. After all, so much can go wrong between start and finish – how can you be sure you picked a winner? Grace Kelly, Ingrid Bergman, Burt Lancaster, Gregory Peck, and John Wayne all went out on (reasonably) high notes. The following nine actors, however, should have quit while they were ahead.
- GENE HACKMAN. Should have retired after: The Royal Tenenbaums (2001). Actually retired after: Welcome to Mooseport (2004). I'm no big Tenenbaums fan, but I'll accept that it's got a strong following and that it will be considered a landmark film for a long time. You cannot say this about the dull-witted comedy Welcome to Mooseport.
- SEAN CONNERY. Should have retired after: Finding Forrester (2000). Actually retired after: The League of Extraordinary Gentlemen (2003). (I'm excluding his recent voice work as "Sir Billi" in a no-budget CG animated curio.) I have not seen Finding Forrester, and I understand that some find it mawkish and lame. But at least it's literate, it has a distinguished director (Gus Van Sant), and it would have made a tender sendoff for the aging Scotsman. (Smarter still: accepting the role of Gandalf in the Lord of the Rings trilogy, which was offered to him.) Instead, Sir Sean bowed out after "LXG", an effects-laden stinker.
- GRETA GARBO. Should have retired after: Ninotchka (1939). Actually retired after: Two-Faced Woman (1941). Although she made her last film at 35, Garbo's departure from showbiz in fact took years. Bad reviews for Two-Faced Woman, along with the horrors of World War II, made her insecure about her worth as an actress, yet there is proof that she planned to star in a prestigious film for Max Ophüls in 1949. That might have been a fine finale for the reclusive Swede, but the project fell apart. Regardless, nobody could argue that the trivial Two-Faced Woman was any match for Garbo's penultimate film Ninotchka, an undisputed classic.
- BETTE DAVIS. Should have retired after: The Whales of August (1987). Actually retired – well, died – after: Wicked Stepmother (1989). This one's a bit unfair; if Davis hadn't died in 1989, she might have squeezed in something better than the truly wretched Wicked Stepmother. Nevertheless, her second-to-last film, the elegant little Whales of August, would have been preferable. (Whales' other stars, Ann Sothern and Lillian Gish, made it their own swan song.)
- CARY GRANT. Should have retired after: Charade (1963). Actually retired after: Walk Don't Run (1966). One could call Charade the Hitchcock film that wasn't directed by Hitchcock. (Stanley Donen made it.) But it's still a nifty semi-classic, costarring Audrey Hepburn in her prime and featuring Henry Mancini's famous theme, and it has a cool early '60s elegance to it. But does anyone remember the trifling Walk Don't Run, in which Grant played matchmaker to a pair of young lovers during the Tokyo Olympics? I thought not.
- MARLENE DIETRICH. Should have retired after: Judgment at Nuremberg (1961). Actually retired after: Just a Gigolo (1978). During the 17 years between the two movies – the first a major Oscar-winning drama, the second a poorly-reviewed obscurity starring David Bowie – Dietrich had only one other screen appearance: an uncredited cameo in 1964's Paris When It Sizzles. Who knows why she picked Just a Gigolo to be her lone return to the silver screen before her death in 1992? Maybe she was a Bowie fan.
- BURL IVES. Should have retired after: White Dog (1982). Actually retired after: Two Moon Junction (1988). You may argue that the tubby actor/singer doesn't belong with these titans, but I say phooey to that. Ives was a great talent, with an Oscar and a Grammy under his prodigious belt, and Samuel Fuller's White Dog is a fascinating, if visually dated, drama. It's worth watching. Zalman King's softcore turkey Two Moon Junction is not worth watching.
- JACK NICHOLSON. Should have retired after: The Departed (2006). Actually retired after: How Do You Know (2010). Is Nicholson retired? That's the million dollar question, but if the actor is truly done, he should have thrown in the towel after his wonderfully sinister turn in Martin Scorsese's Best Picture Oscar winner, instead of farting around in James L. Brooks's rom-com-bomb.
- GOLDIE HAWN. Should have retired after: Everyone Says I Love You (1996). Actually retired after: The Banger Sisters (2002). Hawn was still fetching, at 50, in Woody Allen's sweet if uneven musical (and also in The First Wives Club, released the same year); her dance number along the Venice canal is charming. But she followed it up with a trio of forgettable flops, concluding with The Banger Sisters. Like the other living actors on this list, there's always a possibility of a comeback. But I'm guessing not. (2017 postscript: Hawn did make a comeback, playing Amy Schumer's mother in Snatched, and probably shouldn't have.)