Woodrow Tiberius Boyd (Woody to his family and friends) is a big-hearted innocent making his way in a world filled with hard-hearted cynics. A man of humble means, Woody was born and raised in Hanover, Indiana, a conservative farm town known for its love of beer.  He comes from a large farming family, comprised mostly of his numerous uncles. He learned a lot about beer growing up in Hanover, and after high school Woody pursued his dream of becoming a bartender in the big city by shot gunning his resume to various big city bars. One made its way into the hands of Cheers’ bartender, Ernie "Coach" Pantusso, and after a time, the duo struck up a correspondence.

The gang first meets Woody when he arrives at Cheers on a trip to meet his long distance mentor. Sadly, his visit coincides with Coach’s untimely death. Sam, seeing how eager he is, decides to give the kid a break, and offers him Coach’s job. Although he’s not the sharpest knife in the drawer -- and much like his mentor, can’t always keep up with the boisterous barroom banter -- his anecdotes of life in Hanover and chipper attitude make for easy admission into the Cheers family. When he’s not working at the bar, Woody is busy participating in community theater productions and working as an extra on a few productions being shot in Boston, like Spenser: For Hire. His first big “break” comes when he lands the part of "Veggie-Boy" in a vegetable juice commercial.

Serially monogamous (unlike his boss), Woody’s first love is hometown sweetheart, Beth Curtis. They try the long distance thing, but in time she marries someone else. Next, Woody courts a widowed, older patron named Mary, even proposing marriage, but she turns him down. Woody meets his future bride, Kelly Gaines -- the pampered, sweet, dim daughter of wealthy Lillian VP, Walter Gaines -- when The Lillian Corporation takes over the bar. He woos her by writing the infamous and hilarious “Kelly Song” for her, but they don’t have an easy time of it as a couple thanks to her interfering father, who thinks the simple farmer isn’t good enough for his little princess. Love prevails, and Woody and Kelly marry and have a child together.