If you own a copy of David D. Neilson's dissertation Society at War: Eyewitness Accounts of Sixteenth Century Japan, you know there is ton of juicy information. Today, I would like to share with you a story about young Hideyoshi.
Neilson (p.99) Source Bukoyawa?
"When Kyuan-sama (=Kitsuno, Nobunaga's wife/concubine), was in Ikoma Yashiki, he stayed close to her and kept her entertained (lit. flattered), her. Because he was good at talking, even in front of her, he unashamedly told sexual stories which usually, people [would] have difficulty telling [in front of such a refined person]. Once, when Lord Nobunaga came to Ikoma yashiki, Tokichiro was called before him to keep him company. Tokichigi (=Tokichiro=Hideyoshi), did not hesitate even in front of Lord Nobunaga., and as usual, told comical stories with many [hand] gestures which pleased Lord Nobunaga. Although he was small, he directly asked Nobunaga to hire him. Hachiemon, who happened to be present, could not help but say; 'Who the hell do you think you are? A little guy like you doesn't have the physical strength [necessary to be a soldier], and your sword technique is doubtful [as well].' Hachiemon tried to placate him, but Tokichiro asked Kyuan-sama to intercede with Lord Nobunaga on his behalf, saying 'I will do anything, even caring for the horses (umano kuchitori).' Her (Kitsuno-sama's) attendant recommended him to Lord Nobunaga. He became a courier for messages between villages (guson, lit. errand boy), [in Owari] and performed smartly. He finally ended up working in Kiyosu Castle. This was the beginning [of Hideyoshi's meteoric rise]."
Tenka no tame!