The main connection is that both directors have a group of actors they've worked with repeatedly, as in the "frequent collaborators" section of their Wikipedia page. That's common for a lot of directors; Quentin Tarantino with Samuel L. Jackson and Uma Thurman, John Hughes with Molly Ringwald and Anthony Michael Hall, Tim Burton with Johnny Depp and his now ex-wife Helena Bonham Carter. The difference, in my diseased mind, is that Apatow and Whedon's collaborators (a word which here means "anyone who has worked with the director several times or had major roles in at least one venture") have a tendency to work together on other projects. This theory focuses on two television series that were quite popular in the height of Whedatow in the late '00s, Bones and How I Met Your Mother.
Bones stars David Boreanez as one half of a crime solving duo. Boreanez also worked with Whedon for seven years as Angel in Buffy the Vampire Slayer and its spinoff Angel. In its third season Bones introduced John Francis Daley, geek Sam Weir of Apatow's Freaks and Geeks, as psychologist Lance Sweets. Carla Gallo, who has appeared in several Apatow films but is most famous for her role in his second "cancelled too soon" series Undeclared, plays Sweets' love interest. Also, Bones' entomologist Jack Hodgins is played by T.J. Thyne who appeared with Boreanez in three episodes of Angel. On a related note, Daley wrote the upcoming film Vacation starring Christina Applegate, who was in both of Apatow's Anchorman films, and features Chris Hemsworth, who of course worked with Whedon on the Avengers films and Cabin in the Woods.
In a way How I Met Your Mother is the centerpiece of Whedatow. It features a marriage between Whedon and Apatow's frequent collaborators. Jason Segel and Alyson Hannigan play "perfect couple" Marshall and Lily. Segel starred in both Freaks and Geeks and Undeclared and has worked with Apatow on four different movies. Hannigan starred in Buffy the Vampire Slayer as Willow Rosenberg. HIMYM also stars Cobie Smulders and Neil Patrick Harris, who have worked with Whedon on the Avengers films and the web series Dr. Horrible's Sing Along Blog respectively.
Then there's James Gunn's live action Scooby-Doo movies. Sarah Michelle Gellar, the titular Buffy of Vampire Slayer, plays Daphne (the purple one) and Linda Cardellini, the titular main freak of and Geeks, plays Velma (the orange one). Scooby-Doo 2: Monsters Unleashed also features Seth Green and Tim Blake Nelson who appeared in Whedon's Vampire Slayer and Apatow's Heavyweights respectively.
It's not unheard of for one of Judd's collaborators to appear in one of Joss's projects or vice versa. Felicia Day, who starred in Dr. Horrible and appeared in Buffy, was in one episode of Undeclared. Linda Cardellini recently made a surprise appearance in Avengers: Age of Ultron. Amy Addams, the romantic lead in Apatow's Talladega Nights, was also in an episode of Buffy. Alan Tudyk, the best part of Firefly and most things he's in, had a small role in Apatow's Knocked Up. David Krumholtz, who worked with Apatow in Freaks, Undeclared, Superbad, and Walk Hard appeared as exposition wizard Mr. Universe in the Firefly sequel movie Serenity. Danny Strong, who appeared in 29 episodes of Buffy, has been in 2 episodes of Girls which is produced by Apatow.
This goes all the way back to the early days of Joss and Judd's careers in the late 80's and early 90's. As far as I can tell the closest the two ever came to working on the same project is their connection to Roseanne Barr. A popular piece of pop culture trivia is that Whedon wrote a few episodes of Barr's landmark sitcom Roseanne, but a less documented fact is that Judd started his career by writing jokes for Barr's stand-up.
Maybe the strangest part is that neither has hardly ever acknowledged the other. I've been on Twitter for a long time and I follow a lot of celebrities, including the "J-vowel-double-letter-duo" as I affectionately call them. It's pretty common for famous people to tweet about whatever TV or film they're enjoying at the time, whether they have anything to do with it or not. Here are two of the biggest directors in Hollywood with vaguely similar careers and names and tons of mutual acquaintances and neither has every directly mentioned the other's work in any significant way. A Google search for their names only brings up the Roseanne connection, Judd jokingly referencing Buffy The Vampire Slayer, Joss defending The Interview, which Judd was not directly involved in but several of his collaborators were, and some more listicles of course.
I'm not saying Whedon and Apatow have some secret feud. Anything is possible but I have no real evidence that they dislike each other whatsoever. It's much more likely that all this is merely the result of the world being small and strange, but it's even more likely the result of my small and strange brain. For the record, though, I'm pretty on board with an Appatow helmed Buffy the Vampire Slayer relaunch. Or any continuation of Buffy really. Or Freaks and Geeks. Or Firefly. Or The Ben Stiller Show. Or Dollhouse. Or Undeclared.
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