Jeopardy makes an appearance in Boston, and Cliff gets on the show. The Jeopardy! round had all 6 categories Cliff specializes in, such as celebrities or the US Postal Service. But when Final Jeopardy approaches, he loses all his money putting a stupid response "Who are three people that have never visited my kitchen?" and becomes depressed afterwards. Meanwhile someone has stolen Sam's little black book and started ringing all the girls in it.
| Name | Type | Role | |
|---|---|---|---|
| Dan O'Shannon | Writer | ||
| Tom Anderson | Writer | ||
| Johnny Gilbert | Guest Star | ||
| Steven Rotblatt | Guest Star | ||
| Audrey Lowell | Guest Star | ||
| Alex Trebek | Guest Star | ||
| William A. Porter | Guest Star | ||
| Greg E. Davis | Guest Star | ||
| Bernard Kuby | Guest Star | ||
| Andy Ackerman | Director |