This film has everything - laughs, tears, heart. It's a training film on how to make a memorable comedy. And it appears its studio had no faith in it initially, since it was released in the spring of 1995, a time of year when you are not competing with a bunch of blockbusters. It's in good company though. Clueless, another classic, was also released that spring.
"Tommy Boy" Callahan (Chris Farley) is a goof off and a screw up from childhood. It takes him seven years to graduate college, with a D average. But his dad "Big Tom" Callahan (Brian Dennehy) welcomes him home with pride and open arms. He gives Tommy an office at the family company, a manufacturer of auto parts. Tommy is always getting sideways with Richard (David Spade), Big Tom Callahan's right-hand man. Richard worked his way up in the company, considers Big Tom to be the father he never had, and he resents Tommy because everything is handed to him - the company, a great dad - and he doesn't seem to appreciate any of it.
And then Big Tom dies suddenly, while he was in the process of expanding the company product line, so an extension in a loan is needed from the bank. But, to the bank, Big Tom WAS the company, and they really don't have faith in it without him. Tommy offers to put up his entire inheritance as collateral if the bank will give them a certain amount of time to get a large number of new sales, to prove the company still has a reputation outside of Big Tom's name. So this launches the lion's share of this film. Tommy, the neophyte who has never really had to work for anything, with Richard, the guy who has had to work for everything - on the road together, in Richard's prize car, trying to make the sales that will save the company.
Speaking of that car, I've always loved the symbolism of Richard and his car. In the beginning of the movie, he is all about his car since it is really the only thing in his life since he has no friends. He employs a no eating rule in the car and is upset when M&Ms roll into his dash. As the movie goes along his car just keeps getting more and more trashed and he cares less and less. His relationship with his car is inversely proportional to his friendship with Tommy. This all climaxes when he is fully sold on helping Tommy by going to ridiculous lengths. When they arrive at the airport near the end, and the parking attendant tells Richard that he can't park his car there, he just throws him the keys and says "keep it." Symbolically trading his car for his friend.
I'd highly recommend this, even if on the surface it might seem like just another sophomoric comedy, because it is not.
