We've had a few party portraits over the years, but the only one I have access to right now is one from Champions with our extended (early) team.
Just for the record, that's: Lady Polarity, Shadow Lord, I forget, Mr. Invulnerable ("Mr. I"), forgot the sorceress with her giant ferret, Particel, Mist, Ed's ninja with Shadow somewhere in his name", Lacquer, Jedi Knight, someone who left before I joined, Pholtus Son of the Sun, Swashbuckler, Atteremi, Warhawk, and Major Weaponry. Not bad for close to 3 decades ago.
In our current group we have a freelance artist who makes his living doing portraits and such. Since it's work and not hobby there's that "hey, do free work for us" stop. Though he did say that if we wanted character portraits he'd do them cheap and several of us took him up on it, and he's done a few roughs of all of us together just to get sizing and everything. It's really cool how he's making them look like our characters - but at the same time making them recognizable as us.