Chris Penn and Michael Madsen have both co-starred with Nicholle Tom. Penn in Beethoven's 2nd (1993) and Madsen in Season of Change (1994).
Along with Reservoir Dogs (1992), Mulholland Falls (1996) and The Florentine (1999), Papertrail (1998) is another film which Chris Penn and Michael Madsen are in together. In fact if it's alternate title Serial Cops is used, then The Florentine is the only film title - co-starring Penn and Madsen - where the second word doesn't end with an s.
Chris Penn's character is called Jason Enola in Papertrail (1998). Enola is the same name of the little girl played by Tina Marjorino in Waterworld (1995), which starred Kevin Costner. Papertrail's Michael Madsen co-starred with Costner in Wyatt Earp (1994).
When we first see FBI Agent Jason Enola (Chris Penn) and FBI Agent Brad Abraham (Michael Madsen), Abraham finds it hard to get together with Enola. Enola is on the phone in his apartment when Abraham knocks on his door, then he's phoned on his cellular phone by a colleague. "What?!" he snaps when he answers. "Brad, are you with Jason in his apartment?" [sarcastically] "Yeah we're in there drinking coffee together! Come on Jason, open the fucking door!" Upon learning something from Jason, "I've been speaking to my ex-wife and she wouldn't let me speak to my two little girls". [Brad insensitively] "Why do you put yourself through this shit?" Clearly Abraham and Enola weren't seeing eye to eye at this early stage.