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There are 8 clues with the answer 'HOWWILLIKNOW'
# CLUE
1.
Number-one hit by Whitney Houston which won the Best Female Video at the MTV Video Music Awards in 1986: 4 wds.
2.
Whitney Houston's second US number-one single, released in 1985 (3,4,1,4)
3.
'86 Whitney Houston chart-topper
4.
1986 Whitney Houston #1 song that asks a question: 4 wds.
5.
1986 #1 hit for Whitney Houston
6.
Song Whitney Houston took to #1 after Janet Jackson passed on it
7.
1986 Whitney Houston chart-topper
8.
A Whitney Houston smash from 1985 (3,4,1,4)