Five degrees of Marvel Movie characters...
... In the sense that there's a semi six degrees of Marvel movies in this film.
What, exactly?
First the no brainer:
Chris Evans and Anthony Mackie: Cap and Falcon.
Second, Topher Grace: Eddie Brock/Venom
Who starred in the movie "In Good Company" (2006) with Clark Gregg, or Agent Coulson of Agents of SHIELD. That movie also starred Topher's love interest, Scarlett Johansson.
The following year, Johansson plays the lead in the film "The Nanny Diaries" (2007), which costars Chris Evans.
Johansson's mother here is played by Donna Murphy, who played Doc Ock's wife in Spider-Man 2 (2004) three years prior.
Ioan Gruffudd - Reed Richards/Mister Fantastic (Fantastic Four 1+2 2005/2007) -who starred alongside Chris Evans' Johnny Storm/Human Torch- appears in this "Playing it Cool" film, along with Co-star Michelle Monaghan.
Michelle Monaghan costars in Robert Downey Jr's film "Kiss Kiss Bang Bang" (2005), which was directed by Shane Black, who also directed Iron Man 3.
What most people don't notice in that film is an awesome Marvel movie reference Six years prior to its release.
In a scene early in the film, Michelle Monaghan's character looks through some books. In the stack you can see a black hardcover with the title "THOR" in red letters and in the exact same font displayed in the film's title which was released in 2011, and directed by Kenneth Branagh.
Branagh, who starred in the 1993 film "Much Ado About Nothing" as Benedick, quotes "...were I duller than The Mighty Thor!" A character whose comics Branagh read thoroughly as a child.
Robert Downey Jr of KKBB costarred with Spiderman's Tobey Maguire and Ant-Man's Hank Pym in Wonder Boys (2000)
Michael Douglas starred in Ghosts of Girlfriends Past (2009), which costars Emma Stone of The Amazing Spiderman 1+2 (2012/2014). Paul Giamatti cameos as a variation of The Rhino in the latter of the two.
Giamatti also appears in The Negotiator (1998) which stars Samuel L. Jackson.
Samuel L. Jackson stars in SWAT (2003), which also stars Jeremy Renner (The Avengers, Avengers: Age of Ultron) and Colin Farrell (Daredevill, 2004)
Daredevil (2004) also features Michael Clark Duncan as the Kingpin. He appears in the Michael Bay film "The " which star Scarlett Johansson and Sean Bean.
Sean Bean, known for many a death in many a film, falls dead in Ca$h (2010) to the close aim of Chris Hemsworth's character Ryan.
Chris Hemsworth- known as adult Thor- has a young version of Thor- Dakota Goyo- who starts in the film Real Steel (2011), starring Hugh Jackman (Wolverine) and Anthony Mackie (Falcon). Hope Davis (Maria Stark, Captain America 3: Civil War) appear as Hugh's ex-wife. Kevin Durand is Juggernaut in the Wolverine (2009) film.
Evangeline Lilly (Ant Man, 2015) stars as Jackman's love interest. James Rebhorn (The Talented Mr. Ripley, 1999) also appears.
Gwyneth Paltrow (Iron Man 1-3, The Avengers) appears in the Ripley film with Cate Blanchett (Hela in Thor: Ragnarok, 2017). Philip Baker Hall does too. Hall also starred in the film Magnolia (1999) which features a cameo by Thomas Jane (The Punisher, 2004).
[*Side note: Paltrow (Pepper Pots) stars with Hope Davis (Maria Stark) and Anthony Hopkins (Odin) in Proof (2005)]
Jane appears with Rosario Dawson (Daredevil 2015/2016) in the film Rent (2005), which features Jesse L. Martin (Law & Order).
Jesse L. Martin plays supporting character in Puncture (2011), which also stars Chris Evans.
Jane appears as Vegan Police with Chris Evans' Evil Ex #3 in Short Pilgrim vs. The World (2010), filmed by Edgar Wright, who was attached to Ant-Man (2015).
Lilly- who appeared as Hope van Dyne in that film, stars with Renner and Mackie in The Hurt Locker (2008).
Chris Evans and Anthony Jackie star in Captain America: Winter Soldier (2014).
Which brings us back to this film, Playing it Cool, where Mackie and Chris Evans star.