"shadiest" in the adjective sense
1. shady
quiet, dark, or concealed
"her shady past intrigued him"
"a shady part of town"
2. fishy, funny, shady, suspect, suspicious
not as expected
"there was something fishy about the accident"
"up to some funny business"
"some definitely queer goings-on"
"a shady deal"
"her motives were suspect"
"suspicious behavior"
3. shady
of questionable honesty or legality
"He established a dummy company through which he laundered vast sums of cash from shady middlemen and arms dealers"
4. shady, shadowed, shadowy, umbrageous
filled with shade
"the shady side of the street"
"the surface of the pond is dark and shadowed"
"we sat on rocks in a shadowy cove"
"cool umbrageous woodlands"
Source: WordNet® (An amazing lexical database of English)
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