Tom Gregory has it all: the house, the cars, the clothes, the assistant?! Tom makes the mistake of hiring a new assistant "Andy" to make him hip; turns out Tom quickly finds he is the new Beverly Hillbillies!
Tom arrives at the Art Gallery to see that nothing is being done and his manager, Junior, is no where in sight. Tom's personal assistant, Andy, shows up to "help out"...
Andy arrives at Tom's house to take him to the big opening of Gregory Way Gallery in Beverly Hills. Andy realizes that Tom's party outfit is not up to par and he decides to make some stylistic adjustments.
It's the official opening of Gregory Way Gallery, and Tom and Andy arrive to find a packed house. As Andy starts to drink more and more, he finds out that Tom isn't giving him credit for his amazing outfit, and plots retribution...
Andy, Tom and Dan decide to take a road trip to Vegas to see their good friend Reuben fight in the UFC at the Palms. Tom reminds them he has obligations in the morning, and Andy tells Tom and Dan to "stay cool."
Tom, Andy, and Dan finally arrive in Las Vegas. As soon as they arrive at their hotel suite, they open a bottle of liquor and propose a toast to a night they will never forget.
Tom, Dan and Andy have finished watching their friend fight in UFC. They are about to go to bed, so they can wake up early and head back to Los Angeles, when Andy tries to talk Tom into hitting the strip.
After their stint in Vegas, the Gregory Way crew decide on some R & R with a scenic route through the beautiful Utah mountains. They then head into their third city to continue the quest for Dorothy, Denver.
After a great Denver experience, the troupe decide to take a few days of R&R and relax in the countryside. After a wild white water rafting trip, the guys argue about who tipped the boat.
After almost drowning, the guys decide to head up the mountain and find some grub. As always, Tom manages to find himself in some drama with the locals.
Andy and the crew arrive in Chicago and stay at the low end Red Roof Inn. Andy decides it's time to have an intervention with Tom, who shoos him away. Tom takes a late night flight to Dallas and is blown away by what he sees in Texas.
After site seeing downtown Chicago, the crew holds auditions. When the group of girls ends up being a disappointment, Andy and Dan put on a little play of their own.
On the way to St. Louis, the Gregory Way RV encounters some misfortune and breaks down on the side of the road. Tom starts doing damage control and aims the blame at a certain somebody.
After Tom is late to host the St Louis auditions, Dan steps in as the emcee and gets his moment to shine. But when Tom shows up, the two divas are reluctant to give up the microphone and decide to host the show together.
The guys take a break to hit up Graceland and then head south to New Orleans. After partying on Bourbon St., Tom and Andy break into a historic cemetery and snoop around.
The next stop on the tour is Jacksonville, and Tom and the gang are talked into checking out a local club called "Metro" by the owner Jerry. Drinks are on the house, and Tom cuts loose.
This is the moment everyone's been waiting for (sort of) The New York Finals. The top 4 girls are brought together on stage and the winner is announced.
Tom is hit with some life changing news, he walks outside to get some air and sees John in his backyard painting. But then he notices something else about John.
Dan comes up with a great idea to host a story night at Gregory Way Gallery. When he arrives the night of the event, he realizes the store manager is no where to be found, and he is locked out with out a key.
Andy and Tom are enjoying a nice Saturday afternoon eating on the hood of the car in the Hollywood Hills. Then Tom drops the news that he is attending a reading for a play shortly and wants Andy to come and spectate.
