Tim Conway

The Drop 40 is back in business baby, and beloved American entertainment figures from the Johnson administration are gonna pay! Fast on the heels of Doris Day laying down for some final pillow talk, comedian and actor Tim Conway has been court-martialed from McHale’s Navy.

Conway was a radio DJ who was discovered Rose Marie in the early 1960s. She discovered his talent for comic sketches and got him a role on The Steve Allen Show as a featured player. This led to his first major breakthrough: portraying the slapstick Ensign Charles Parker alongside a Drop 40 graduate from back in the day, Ernest Borgnine, in the aforementioned McHale’s Navy.

It speaks to Conway’s talent that he was a star to various generations for various work: in the 1970s he was the breakout performer in The Carol Burnett Show with his “The Oldest Man” character; in the 80s and 90s he was the star of the “Dorf On…” series of straight-to-VHS movies that were an essential for any man over the age of 55 who’d learned how to work the video recorder (and are still clogging up car boot sales to this very day); and in the 00s the zoomers got to know him as the voice of Barnacle Boy in Spongebob Squarepants (for which he was reunited with Borgnine).

He was diagnosed with dementia in 2018, which was accompanied by that beloved institution of deadpoolers: the family fight for his legal rights. His wife beat his daughter to the conservatorship, but there was only ever going to be one final winner here: the DDP as a whole.

Tim Conway
December 15, 1933 – May 14, 2019
Died aged 85 (46 picks, 7 jokers)