Sylvester Stallone, Tom Berenger, Kelsey Grammer, Kyra Sedgwick, Thomas Jane, Kevin Connolly, Omari Hardwick, and Lauren Cohan in Reach Me (2014)

Kevin Dillon, Adrian Grenier, Jeremy Piven, Kevin Connolly, and Jerry Ferrara in Entourage (2004)

John Malkovich, Fred Thompson, Scott Glenn, Kevin Connolly, Margo Martindale, Vin Morreale Jr., Mike Battaglia, Penny Chenery, and Brennan James Callan in Secretariat (2010)

Jennifer Aniston, Drew Barrymore, Jennifer Connelly, Ben Affleck, Kevin Connolly, Bradley Cooper, Ginnifer Goodwin, Scarlett Johansson, and Justin Long in He's Just Not That Into You (2009)

Kevin Connolly, Lucille, Zulay Henao, and Lil Rel Howery in Dashing Through the Snow (2023)

Kevin Connolly and Mark Consuelos in Pitch (2016)

Kevin Connolly and Kate Mara in Entourage (2004)

Kevin Dillon, Emmanuelle Chriqui, Adrian Grenier, Jeremy Piven, Kevin Connolly, and Jerry Ferrara in Entourage (2015)

Kevin Dillon, Adrian Grenier, Kevin Connolly, Jerry Ferrara, and Ronda Rousey in Entourage (2015)

Kevin Dillon, Adrian Grenier, Jeremy Piven, Kevin Connolly, and Jerry Ferrara in Entourage (2015)

Adrian Grenier, Haley Joel Osment, and Kevin Connolly in Entourage (2015)

Adrian Grenier, Jeremy Piven, Kevin Connolly, and Justin Wilson in Entourage (2015)

Adrian Grenier and Kevin Connolly in Entourage (2015)

Kevin Dillon, Adrian Grenier, Kevin Connolly, and Jerry Ferrara in Entourage (2015)

Kevin Dillon, Adrian Grenier, Jeremy Piven, Kevin Connolly, and Jaime Ferrar in Entourage (2015)

Kevin Connolly in Friends with Better Lives (2014)

Leonardo DiCaprio, Tobey Maguire, Marissa Ribisi, Amber Benson, Scott Bloom, Kevin Connolly, Jenny Lewis, and Meadow Sisto in Don's Plum (2001)