In the 90's one of the most popular African American TV shows was the sitcom Martin starring Martin Lawrence. The Martin show came to prominence mostly from the hilarious performances of the leading actor. His ability to play a large variety of characters (Jerome, Roscoe, Otis, etc) easily makes him the funniest and most important character on the show. However, there are reoccurring themes that make the other main characters almost just as funny. For example, Pam and Martin's beef that always leads to name calling such as inch high private eye or insisting that Pam was raised by wolves. There is Cole and Big Shirly's relationship which stirs up constant jokes, and the fact that Cole lives at home with his mother, both are reoccurring themes in the show. The funniest to me is the persistent mentioning of Tommy's lack of a job, and the constant curiosity of what Tommy does for a living. All this reaches its boiling point on episode number 10 on Season 3 entitled "Get a Job". Being that this is my favorite reoccurring theme on the show, I decided to make a top 3 list of jobs Tommy most likely had.
#3 Undercover Cop
Tommy could have been a undercover cop. His secretive nature maybe a part of the necessity to not blow his cover. With Martin being a radio host and Cole's mother being the biggest gossiper in town, his cover could have been blown easily if he were to reveal his position to his friends. Tommy is 6'4 and at least 225 lbs, this would help him take down criminals in Detroit. With two crazy friends like Martin and Cole, why would anyone tell them they are a undercover detective intentionally? With the number of crazy missions those three have been on (going to a little people bar to fight, following Gina to Chicago to see if she's cheating, etc) it would be no time before Tommy is talked into breaking a law and goes to prison. He plays it smart by keeping his job as an officer of the law a secret hidden from his friends, and at times even his girlfriends.
#1 Drug Kingpin
Most likely Tommy had them bricks. He was probably a drug lord like Pablo Escobar, El Chapo, or Griselda Blanco. Like I mentioned before he kept a bank roll on him, a nice watch, a beeper, was well dressed, had to leave late at night to go to "work" and was often seen with a expensive leather jacket on (speaking of the leather jacket, it's a nice place to hold your gun just in case you see somebody you fronted dope to, they are late on a payment, and you have to put in some work). He dressed nice but he wasn't real flashy. Avoiding jewelry and expensive cars, hanging out with regular people, not telling his friends his business and wearing those Steve Urkel glasses all the time was genius. Plus it kept Tommy out the pen while he was supplying Detroit with the highest grade white girl they ever seen before. I don't think Tommy was a regular drug dealer, I think he was like the black Walter White; someone nobody would think was moving weight and never touched it himself but was raking in millions. Both characters kept a low profile but their behavior was so mysterious that it provoked suspicion in their closest of friends.