Bleakest rhymes with:
sleekest, sleekest, weakest, anarchist, blackest, darkest, focused, focussed, locust, refocused, sickest, sleekest, slickest, unfocused, weakest
Bleakest sounds like:
balked, ballast, belched, bellsouth, belsito, bilked, biologist, blacked, blackest, blackett, blackheath, blackout, blackwood, blast, blasted, blazed, bleached, blessed, blest, blight, blighted, blissett, blixt, blockade, blockaded, blocked, blockhead, blowiest, bluest, blushed, blust, bolstad, bulged, bulkhead, bullshit