|Widow Often Annie|
|Original Air Date||October 17th, 1969|
|Writers||Lloyd Turner and Whitey Mitchell|
|Previous Episode||Valerie of the Dolls|
|Next Episode||The Treasure of C. Errol Madre|
Maxwell Smart is ordered to romance Ann Cameron, a glamorous KAOS agent who marries CONTROL agents, insures them heavily and then murders them and turns the money over to KAOS. Coming on the eve of Max and 99's anniversary, and with 99 about to give birth, the assignment understandably causes tension in the Smart marriage.
- Maxwell Smart - Don Adams
- Agent 99 - Barbara Feldon
- Chief - Edward Platt
- Larabee - Robert Karvelas
- Lou (uncredited)
- The title refers to the comic strip Little Orphan Annie, later also the basis for the stage and film musical Annie.