Oddest/ most interesting connection to a role featured on a different show

The Psych episode “Duel Spires” is an homage to Twin Peaks and includes 7 Twin Peaks cast members.

This (and others like this) are crossovers, and I don’t think really fit in the spirit of the OP. Friends, Mad About You, and Seinfeld were set in the same universe and these were the actual characters. Similar to Green Acres, Beverly Hillbillies, and Petticoat Junction.

I think (and please correct me if I’m mistaken) the OP is looking for more subtle or meta references.

Way back when, on an episode T A-Team, the gang was at Universal Studios or a con or something like that, when a Cylon from the original Battlestar Galactic walked by. Face (played by Dirk Benedict, who was Starbuck in BG) stopped in his tracks and stared at the Cylon for a long while.

In “Happy Gilmore”, the character ‘Otto’ (Allen Covert) is dressed and makeup’d to be a dead ringer for Bill Murray in ‘Caddyshack’.

This one goes back a long way, but in the early 1970s the most popular daytime soap opera was NBC’s Another World (AW), and the most popular soap couple (prior to the Luke & Laura phenomenon about 10 years later) was Steve and Alice. They were pitted in a long storyline in which scheming brunette Rachel (played by actress Robin Strasser) was always trying to drive heroic Steve and virtuous Alice apart - so she could have Steve for herself.

By 1975, a new producer (modern day ‘show runner’) took over the show and decided the storyline was played out. That, and the fact that the actors portraying Steve and Alice were both insufferable divas, led to both characters being written out and the actors fired. (Actress Robin Strasser had already left the show, but the actress who took over the part of Rachel became the new star of AW.)

Meanwhile over at ABC, the soap opera One Life to Live (OLTL) which aired in the same time slot as AW was doing so badly in the ratings that it was near cancellation. The producer for that show wasted no time hiring the actors who played Steve and Alice, and introducing them on OLTL. It being a rival network, the show couldn’t call them Steve or Alice, of course; but when “Tony” and “Pat” were introduced, they were explained as having a long, tempestuous history together. “Tony” was then quickly married off to a scheming brunette named Cathy who acted very much like “Rachel” had on AW - constantly jealous and conniving.

In an interview, Actress Robin Strasser later admitted that the producer of OLTL at that time had actually offered her the part of Cathy, in an attempt to completely recreate the Alice-Steve-Rachel love triangle that was so popular on NBC. She wasn’t interested in doing another soap at the time. Later she changed her mind and took over the role of OLTL’s chief bitch character Dorian. The actor who had played Steve / Tony had already quit the show by that time, so OLTL never got the chance to truly “do over” the AW storyline. But when Strasser did debut on OLTL, one of the very first storylines she had was fighting with “Pat” over another man named Clint.

(I’m a little ashamed that I know all of this.)

A couple of times, Criminal Minds has made obscure references to other movies with the names of characters, but I never figured out why: maybe if I post them here, someone else can explain them.

On an episode titled “Unknown Subject,” a serial rapist called The Piano Man is reoffending by victimising again the same women he already raped once. Several of the characters are named for characters in a 1963 movie called Charade that starred Cary Grant and Audrey Hepburn. In another episode, two victims are named Gloria Holden and Marguerite Churchill, which are the names of two Hollywood actresses from the 30s, who both starred in a 1936 film called Dracula’s Daughter; this episode was called “The Black Queen,” which I suppose would be a nice nickname for Dracula’s Daughter, except it’s pretty clear who the Black Queen is, and it’s not Dracula’s Daughter.

Other than the writers throwing in random things just to see if people notice, I can’t figure out if the names mean anything.

On LOIS AND CLARK in the '90s, Jimmy Olsen got zapped by an old-age device.

He promptly turned into Jack Larson, who’d played Jimmy Olsen back in the '50s.

He’s not actually Werner Klemperer. He’s just assuming his form.

On “Married With Children” someone told Ted McGinley’s character that her looked like that guy from “Happy Days”. On “Herman’s Head” somebody told Yeardly Smith’s character that she sounded like Lisa Simpson.

When Tracey Wells, who played Heather on Mr. Belvedere guest-starred on an episode of Growing Pains, one character described her as “looking just like that girl on Mr. Belvedere.”

On an episode of Happy Days, the parents are going to see The Music Man, and the mother says she loves the red-headed boy in the movie, because he reminds her so much of Richie when he was little. The red-headed boy, Winthrop, is played by Ron Howard, around age eight.

ETA: just a couple of weeks ago, Jon Cryer’s Halloween costume is “Duckie, from Pretty in Pink.” Everybody thinks he’s supposed to be Ferris Bueller.

One I’ve always wondered about-- Sherilyn Fenn played a woman with an artificial leg in a Friends episode. (It’s actually one of the show’s funniest moments.) It was just a few years after Fenn appeared in Boxing Helena, and I always wondered if Fenn was cast specifically as a nod to the movie.

In the Nikki Heat books (supposedly written by Castle) there are a couple of cops she works with named Malcolm and Reynolds.

And that episode also had a crowd chasing him because he looked like the photographer from The Love Boat.

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