The Casting Ouch!

Unlikely Private Eyes (No, Really…)

What the hell were they thinking? Sometimes you just have to scratch your head. Some people should just NOT play private eyes. Some of them shouldn’t even act at all.

And yet, all these people, more famous for other things or other roles, have been cast at one time or another as private eyes. Some of them even turned in credible performances.  Who knew?

But most of the others? Ouch!

  • Sonny Bono
    Because, of course, when you think of country music, you automatically think of “Sonny Bono,” right? So who would be better playing Nashville private eye Sonny Hunt in a 1979 TV flick called Murder in Music City
  • George Carlin
    The irritable, prickly comic shows a surprisingly kinder, gentler side in the Disney flick Justin Case, as the eponymous private eye who shows up as a ghost to solve a murder — his own!
  • Andrew Dice Clay
    The notoriously obnoxious and foul-mouthed comedian got to play an obnoxious and foul-mouthed private eye in 1990s feature film The Adventures of Ford Fairlane. Whoa!
  • Tim Conway
    The affable everyman Conway played Ace Crawford, Private Eye in a short-lived series from 1983. A scrupulously honest hard-boiled dick, Ace seemed to have it all — adoring women, a faithful sidekick who idolized him and a beautiful girlfriend madly in love with him. Ace (and the writers) lacked only one thing… a clue.
  • Bill Cosby
    Once upon a time America’s favourite dad (and before that, America’s most beloved jet-setting spy), Cosby played a private eye twice. Once in the amazing, sun-bleached feature film noir cult favourite Hickey and Boggs (1972), co-starring and directed by I Spy co-star Robert Culp, and a few years later in the far less memorable TV series The Cosby Mysteries, where he played retired criminologist Guy Hanks. Neither really damages his reputation now, but then, what could?
  • Bing Crosby
    In the 1949 romantic comedy (with music) Top o’ the Morning, the Bingster plays Joe Mulqueen, a singing insurance investigator dispatched to Ireland to recover the stolen Blarney Stone. As a bonus, while he’s there, he gets to woo the local policeman’s daughter. Blarney, indeed.
  • Miley Cyrus
    So Undercover was a 2012 movie starring the former Hanna Montana, caught somewhere between fast-fading childhood stardom and Wrecking Ball notoriety. When will the madness stop?
  • Mac Davis
    The affable singer-songwriter, best known for penning such soft country hits as “Hell of a Woman,” “Something’s Burnin'” and “Baby, Don’t Get Hooked on Me’ was one of the few on this list to show actual acting chops. After his surprisingly effective acting debut in the big screen football drama North Dallas Forty, he went on to play a private eye not once, but twice. In 1980, he played an obnoxious, skirt-chasing private eye, Bill Dekker, in the equally obnoxious Cheaper to Keep Her, but he was much better as Norm Swallow, a crooked P.I. in Blackmail, a 1991 made-for-TV movie.
  • Sammy Davis Jr.
    A pre-Candy Man Sammy starred as a hip, streetwise dick in The Pigeon, a failed TV pilot. There’s some vaguely coherent business about an ex-girlfriend, a young girl in danger, a missing diary the “Mob” desperately wants and a frame job. But it’s all really just a wink-wink to His Samminess and his rapidly fading Rat Pack cool, which may be enough for some older viewers
    BONUS OUCH: Sammy’s version of the “Theme from Shaft.”
  • Sam Elliot
    Hard to believe, but the affably somnolent drawlfest was cast as John D. MacDonald’s Travis McGee in a 1983 pilot, The Empty Copper Sea, based on MacDonald’s novel of the same name. Yes, it was horrible, but that didn’t stop producers from casting him as a private eye again (and again), in 1986’s Blue Lightning, and in 1993’s Fugitive Nights: Danger in the Desert, based on a novel by Joseph Wambaugh. It wasn’t that Elliot was particularly bad in these (well, he pretty much sucked in Fugitive Nights), but just horribly, horribly miscast.
  • Lorne Greene
    Canada’s own “Voice of Doom” (you may know him as Pa Cartwright of Bonanza) played an LAPD captain who comes out of retirement when his son is murdered and his grandson is kidnapped in the ill-fated 1973-74 TV series Griff.
  • Jim and Jon Hager
    Hee Haw‘s hayseed hunks played Twin Detectives in the TV flick of the same name. It was “as good as it sounds,” says Lee Goldberg.
  • Lauren Holly
    The former Picket Fences star (and former Mrs. Carrey) played a down-home private eye in the 2004 Lifetime movie Caught in the Act.
  • Dennis Leary
    Leary played a bitter, drunken piano player who teams up with a P.I. buddy to put the squeeze on a wealthy businessman in Love Walked In, a 1998 straight-to-video B-noir that has its moments.
  • Jerry Lewis
    TV repairman and doofus Lester March is not exactly a P.I., but he’s definitely P.I.-adjacent in 1962’s It’s Only Money.
  • Dean Martin
    Yeah, Martin played Donald Hamilton’s Matt Helm four times in the movies, and maybe you can make some sort of case for Helm being a private eye of sorts in those films, but I won’t.
  • Jackie Mason
    Goldberg. P.I. was a 2011 movie starring Jackie Mason as Miami-based private eye Jackie Goldberg. Oy vey.
  • Elizabeth Montgomery
    The Bewitched star gave a very convincing performance as recently widowed P.I. Sara Scottinvestigating the murder of her journalist husband in Missing Pieces, a solid 1983 made-for-TV flick.
  • Ron Perlman
    The long-faced one, best known at the time only for Beauty and the Beast, played John “Mac” McClure, the usual alcoholic ex-cop/private eye “bordering on pathetic” in the 1993 straight-to-cable Double Exposure.
  • Joe Pesci
    In Half-Nelson, a short-lived TV series from 1985, Pesci plays an annoying pipsqueak of a private eye who’s set loose in Hollywood. And nobody does annoying like Joe Pesci. Unfortunately for Joe, the show also annoyed viewers.
  • Kenny Rogers
    No coward of the county, Rogers left the comfort zone of country-and-western stardom to try and parlay his celebrity into a regular TV gig as private eye John J. MacShayne in MacShayne: Winner Take All. Sometimes you gotta know when to fold ’em, Kenny.
  • Telly Savalas
    Sure, as Theo Kojak, the lollipop-slurping pride of the NYPD, Savalas ruled. But as Harry Powell, a snoop-for-hire in the 1989 feature film spoof The Hollywood Detective? Meh…
  • O.J. Simpson
    Before he got his own true crime show (aka “the Nineties”), he starred as Fred Zackel’s Michael Brennen in the TV pilot, Cocaine and Blue Eyes, based on Zackel’s novel. The fact that Brennen was supposed to be white and Irish didn’t matter.
  • Frank Sinatra
    Slap a fedora on his head, and put him in a suit-and-tie, and as long as he stayed on dry land Old Blue Eyes was passable as Miami gumshoe Tony Rome. But the moment he boarded The Straight Pass, the 36-foot sports cruiser he called home, all bets were off. Putting a dorky captain’s hat and whiter-than-white sailor duds on Frankie didn’t make him into a believable boatnik, never mind a hard-ass P.I.–he looked more like his mommy dressed him. No wonder the movie posters featured him in the more traditional P.I. fedora and jacket.
  • Shelley Winters
    Played “Big Rose” Winters in a 1974 made-for-TV movie, Big Rose: Double Trouble. It was a pilot.
A work in progress, respectfully compiled by Kevin Burton Smith.

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