Alexander Singer directed more episodes of Lou Grant than anyone else. He also directed several episodes of ST:TNG, ST: DS9 and ST:V. And if you can’t connect those to ST:TOS in one step you don’t belong in this thread.
It seems that you are more towards the “maximizing degrees of separation” rather than minimizing. And if you’re going that way there’s basically no limit.
I can also do a closer connection between TOS and Lou Grant, although not as close as ftg’s. Lawrence Pressman was Lou Grant’s son in law on MTM, and much later Kira Nerys’s Cardassian dad on DS9; from DS9 to TOS you can make any number of connections, but the shortest would be through their respective Tribble episodes.
Star Trek: TOS -> The Tick
Ted Cassidy did the voice of Balok on TOS
Ted Cassidy appeared with John Astin on The Addams Family
John Astin appeared on Seinfeld
Patrick Warburton also appeared on Seinfeld
Patrick Warburton appeared on The Tick
I can do shortcuts too. Jon Lormer was in three episodes of TOS, including “The Cage,” and later in an episode of Lou Grant (after making appearances in MTM, Rhoda, and Phyllis).
The point is to be creative. Call it “maximizing,” if you want. Use your imagination and make connections like John Burke.
Star Trek TOS-> Magnum PI
Ted Cassidy as voice of Balok
Ted Cassidy and John Astin on Addams Family
John Astin on Mad about You
Lisa Kudrow on Mad About You and Friends
Tom Selleck on Friends
Tom Selleck on Magnum PI
(Was pondering ecdysiast Blaze Starr and Robert Wuhl the other day and realized this cycle.)
*The Great American Dream Machine was an amazing public TV series back in the 70s. One segment was about …
Blaze Starr. Blaze wrote an autobiography that was made into the movie … Blaze. The title character was played by …
Lolita Davidovich whose husband …
Ron Shelton wrote and directed … Bull Durham, one of the players in it was …
Robert Wuhl, who got his first big gig in … The Hollywood Knights which also had in it …
Leigh French who was best known for appearing on …
*The Smothers Brothers Comedy Hour which had another cast member, the late great …
Bob Einstein who was the brother of …
Albert Brooks who did some really funny stuff on …
*The Great American Dream Machine.
So one longish path and one short one between TGADM and TSBCH depending on your preference.
(I think according to Bokonism this would make all these people members of a granfalloon.)
The internet has made games like this a little too easy. I may not have the optimum link, but I prefer to see what solutions I can come up with from memory alone.
So here’s one for y’all: Sesame Street to The Rockford Files
My solution:The cast of Sesame Street included Jim Henson
Jim Henson was on The Muppet Show
The guest star on one episode of The Muppet Show was Rita Moreno
Rita Moreno guest starred multiple times on The Rockford Files
Now, for the really clever bit, what does every link in my chain have in common?
Every link won an Emmy. Henson won Emmys for Sesame Street (a daytime Emmy) and The Muppet Show; Rita Moreno won her two Emmys for her appearances on The Muppet Show and The Rockford Files.
Trying to pull two really different titles from my head, I went with I* Married Joan* and The Santa Clarita Diet.
Jim Backus starred on I Married Joan.
Backus starred with Alan Hale Jr on Gilligan’s Island.
Hale guest-starred on The Andy Griffith Show.
Ron Howard guest-starred on The Simpsons.
Drew Barrymore guest-starred on a different episode of The Simpsons.
*I Married Joan *had 3 appearances by Sheldon Leonard. (Yes, that guy.) He had an appearance at … The 46th Annual Director’s Guild Awards. A winner that night was Steven Spielberg who directed … E.T. the Extra-Terrestrial. Starring Drew Barrymore who is in … The Santa Clarita Diet.
(With Sheldon Leonard at one end and Spielberg at the other, you can pass thru all sorts of shows along the way. E.g., a longer path goes thru The Don Rickles Show and Night Gallery via Louise Sorel or some such.)