| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| Long associated with the riding-the-rails hobo lifestyle, he's the legend heard here | Boxcar Willie | $2,000 | DJ | WORKING ON THE RAILROAD | 2014-10-02 | #6909 | |
| In 1987 this "World's Favorite Hobo", known for songs of riding the rails, opened his own theater in Branson | Boxcar Willie | $600 | DJ | TRAINS | 2000-04-10 | #3601 |