Initially, both celebrities were each given two phrases to relay to their partners by drawing. There was a connecting word in both phrases. If they were both successfully guessed, the civilian contestant won $200. After both teams had taken a turn, a second set of phrases was played. Later in the series' run, the round was modified slightly. This time, the celebrities drew as many phrases as they could in the time limit and each correct guess paid off at $100.
Round 2
Players took turns drawing a series of puzzles for three minutes. This time, each puzzle had a different connecting word. Correct answers were worth $100, and if the team was stumped the player at the drawing board could pass the marker off to one of his/her teammates. The team in the lead played first, followed by the opposing team. The team with the most money at the end of the round won the game and advanced to the bonus round. If both teams were tied, Thicke would draw a tie-breaking puzzle, with the first team to answer correctly becoming the winner. Regardless, both teams kept their money.
Bonus Round
In the bonus round, one team member was selected by his teammates to draw single-word puzzles instead of phrases for this 90-second round. Each word was connected to the word before it in chain fashion, such as Peanut-Butter-Bread-Basket-etc. The first four words were worth $100 each. The next three that followed would be worth $300. Every word after that was worth an additional $1,000. Play stopped when the timer ran out and the civilian player won whatever money the team had accumulated. Originally, there were returning champions, who remained on the show until they were defeated or reached the Friday show of any given week. Within two months, however, they were dropped altogether, and two new contestants competed on each show.
Bloopers
Pictionary is famous for an incident involving Erik Estrada and Bill Maher, which has since made the rounds on blooper reels. An enthusiastic Estrada was attempting to solve the puzzle — "Tie a Yellow Ribbon 'Round the Old Oak Tree." Upon getting the right answer, he raised his fists in celebration, unaware that Maher was close behind him, and ended up punching Maher square in his nose. Taping had to be stopped while a paramedic attended to Maher, but resumed after it was determined Maher's injuries were not serious.