There is the sign writer who was making a new sign for the pub the "Dog And Duck" but got the words too close together for the owners tastes, so he complained that "The spaces between Dog and And and And and Duck are all too small"

I'm sure there is a fairly long one involving complex but I can't remember it, something to do with a complex (difficult) complex (complicated) complex (collection of similar buildings) complex (abnormal mental state) so like "I have a complex complex complex complex" whereby I have a hard for psychiatrists to help with abnormal mental state relating to collections of similar buildings which are arranged in a complicated manner... But I'm sure it could be taken to more than four complexes, just can't remember it all.

And of course had arch bishop Desmond TuTu decided to give his aides a day off work, and should two of his staff have been having an affair and wanted to synchronise their breaks, but also time it to coincide with getting a train to the destination of the romantic interlude whilst maximising time there hence picking a very specific 24 hour window as their 'day' off, for which the first one requested 1:58pm one day until the same time the next time, and the other followed up with "I'll please have from two to two to two to two too tutu"