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There are 5 clues with the answer 'DAVIDLETTERMAN'
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CLUE
1.
TV host with a Top Ten List
2.
Postmaster General (TV personality)
3.
Late-night host mentored by Johnny Carson
4.
Talk-show host who retired in 2015 and unretired in 2018: 2 wds.
5.
Talk show host who retired in 2015 after 6,000 episodes; he un-retired three years later with another talk show