Enjoyable 80s detective drama set in San Diego, California. Brothers Rick and A.J. Simon are partners in a private detective agency. They are polar opposites: bad boy Rick is a street-smart former Marine and Vietnam vet who has friends in low places and a love for cheap pleasures; golden boy A.J. is a book-smart college graduate, a former Vietnam protester (he wanted his big brother to come home safe) whose tastes run to the more upscale. Rick drives a beat-up old pickup truck, adheres to a casual dress code (including his ever-present cowboy hat) and lives on a boat parked on a trailer in A.J.'s yard with his dog Marlowe; A.J. drives a series of classic sports cars, has a yuppie wardrobe and lives in a tasteful little house near the water.
This show provides examples of:
- Affectionate Parody: The show was the subject of the first [adult swim] special The Greatest Event In Television History
- "Awesome McCool" Name: One episode had the brothers chasing a computer hacker-turned-electronic bank robber who called himself "Anthrax Vermilion". Rick Simon off-handedly remarks that its a perfect "action hero name" as long as you don't think of the meaning (anthrax being a deadly disease, vermilion being a shade of the color red). It's subverted in the fact that it turns out that "Anthrax Vermilion" is a nine-year-old boy played by Robbie Rist.
- Big Brother Instinct: Even though Rick is the older brother, both brothers exhibit this trope on occasion.
- Black Best Friend: Downtown Brown, one of the coolest police lieutenants on TV, ever. Say it with me now—Town: "Raise your right hand and repeat after me: 'We're deputies.'"
Simon Bros.: "We're deputies."
Town: "You're deputies."
- Cool Car: Rick had his Dodge Power Wagon, and AJ had a series of them: a 1957 Chevrolet Bel Air convertible, later a customized Chevrolet Camaro Z28, and then a 1968 Chevrolet Camaro RS convertible in a two-part episode ("Pirate Key").
- Cool Guns: Rick has a .44 Magnum and A.J. has a .357 Magnum revolver.
- Crossover: With Magnum, P.I.. First the Simon Brothers appeared on Magnum, and then Higgins appeared on the following Simon and Simon episode.
- Also with the nearly-forgotten show Whiz Kids.
- Ditzy Secretary: In an episode where the brothers were trying to incorporate their agency, including an office and secretary, they passed over a rather dumpy middle-aged looking woman who had an impressive resume for a young and beautiful, but very Dumb Blonde who didn't even have the sense to answer the phone when it rang.
- Dramedy: Comedic elements include brotherly bickering, but Rick's history as a Vietnam vet (who is depicted in one episode suffering from service-related nightmares) is among the darker aspects of the show.
- Detective Patsy: The brothers were hired by a magician into a case, and they discover that the ex wife of the magician did it. Later, they discover it was all the magician ruse. Then he explains:So it was just like a standard Stage Magician trick: You guys are the public, you must be smart enough to figure out the distraction, but not smart enough to discover the real trick.
- Happens three times in the first season episode "Ashes to Ashes, and None Too Soon". A woman hires the brothers to serve a man with a subpoena, but the man isn't who she said he was. They soon get a visit from a woman claiming to be the real man's ex-wife; she's not who she claims to be, either. Everybody ends up being investigated by a Customs agent, who is who he says he is, but has something going on the side.
- False Reassurance: Rick is infiltrating a pagan witch coven on a job when the leader of the coven says he's discovered that Rick is a P.I. Rather than try to deny it, Rick says he is and starts handing out business cards, saying it's his day job. The woman who recruited Rick to investigate the coven points out that they come from all walks of life, so why not a P.I.? It works on most of the coven but the leader is still suspicious. As he's the bad guy, he has ample reason to be.
- Friend on the Force: Assistant D.A. Janet Fowler in the early seasons, followed by Downtown Brown and then Lt. Abigail Marsh for the last two.
- Guile Hero: Both brothers operate via small-time cons most commonly.
- Hired for Their Looks: When the brothers hire a secretary, they look at the first one, a grandmotherly looking woman with an impressive resume, but go with a beautiful blonde who doesn't even have enough sense to answer a ringing phone.
- Horrible Hollywood: Rick Simon routinely refers to Hollywood as "Hollyweird".
- Knockout Gas: In the episode "Under the Knife" has A.J. gassed in a hospital room and in danger of unnecessary surgery when the brothers get too close to the truth in a malpractice scam. Also, in the Halloween Episode "The Skull of Nostradamus," both brothers and their dog are gassed by the bad guys who, for some baffling reason, steal their clothes and leave them unconscious in caskets that have been lowered into open cemetery graves.
- Naked People Are Funny: "The Skull of Nostradamus," mentioned above, hints at this, since the brothers are stripped by the bad guys and left naked except for thin white sheets. But the show goes all in with "The Bare Facts," an episode set almost entirely at a nudist colony, where nearly every aspect of this trope is explored. Another episode, "Sunrise at Camp Apollo," was set at a youth camp where the two brothers had a brief prank war that culminated in Rick having his clothes stolen while he was showering.
- Name and Name: Same and same.
- Pretty in Mink: Once they helped a fashion designer who wore a lynx coat in a few scenes.
- Private Detective: The brothers' line of work.
- Red Oni, Blue Oni: Rick is red, A.J. is blue.
- Reunion Show: 1995's TV movie Simon & Simon: In Trouble Again.
- Super Serum: an investigation of a series of mysterious deaths at a nearby college campus reveals the testing of an experimental serum to be the culprit.