6. Knocked Up (2007)
The 2000s saw the rise of a new brand of off-kilter comedy from the Judd Apatow class, with the likes of Seth Rogen, Jason Segel and Jonah Hill rising to the top of the industry. In Knocked Up, Apatow was able to forge a cast of all of the names he is most associated with, the now many-award-winning cast of names including the three mentioned above, Ant-Man Paul Rudd, How To Train Your Dragon’s Jay Baruchel, Spider-Man: Homecoming’s Martin Starr, Kristen Wiig, Bill Hader, Rogue One’s Alan Tudyk, Adam Scott, Craig Robinson and even Ghostbusters (2016) director Paul Feig.
In retrospect, this truly is a who’s who of would-be superstardom, each name making Knocked Up just that little bit better than it may have otherwise been.
Cast: Seth Rogen, Katherin Heigl, Leslie Mann, Paul Rudd, Jason Segel, Jay Baruchel, Jonah Hill, Martin Starr, Kristen Wiig, Harold Ramis, Ken Jeong, Charlyne Yi, Bill Hader, Alan Tudyk, B.J. Novak, Adam Scott, Craig Robinson, Paul Feig
7. Chasing Amy (1997)
Basically the 90s version of Knocked Up because of how its cast would come to define an entire decade’s worth of cinema, Kevin Smith’s Chasing Amy was very much in-keeping with the screenwriter-director’s sensibilities and thus cast most of the filmmaker’s closest cinematic allies, including Oscar winning screenwriters Matt Damon and Ben Affleck (whatever happened to them?), Jay & Silent Bob partner Jason Mewes, Jason Lee and would-be Oscar winning actor Casey Affleck.
An entire sub-category of cinema was painted for the masses in Chasing Amy, encapsulating a part of the 90s only very particular groups will associate with for one of the most star-studded rom-coms of the modern era.
Cast: Joey Lauren Adams, Ben Affleck, Kevin Smith, Jason Lee, Jason Mewes, Matt Damon, Scott Mosier, Brian O’Halloran, Casey Affleck, Ethan Suplee, Jeff Anderson
Recommended for you: 10 Best Matt Damon Performances
8. Trainwreck (2015)
The Judd Apatow directed and Amy Schumer written Trainwreck truly did everything to bring the rom-com back in 2015, leaning heavily on its comedic aspects to provide us with some of the very best cameos we could have imagined, including an angry Daniel Radcliffe walking his troop of dogs and a homoerotic John Cena providing each of us with many, many laughs.
As well as Schumer, Radcliffe and Cena, Trainwreck featured prominent roles for Bill Hader and Oscar-winner Brie Larson, with the likes of Ezra Miller, Randall Park, Matthew Broderick, Marisa Tomei and even the great Tilda Swinton each making an appearance.
It seems that Apatow attempted to move one step beyond his achievements with Knocked Up in establishing this ensemble, arguably the deepest on this list.
Cast: Amy Schumer, Bill Hader, LeBron James, Brie Larson, John Cena, Vanessa Bayer, Tilda Swinton, Colin Quinn, Ezra Miller, Daniel Radcliffe, Pete Davidson, Randall Park, John Glaser, Marisa Tomei, Claudia O’Doherty, Leslie Jones, Matthew Broderick, Tim Meadows