In spite of the fact that he fought in the battles of Badr, Uhud, Khandaq and other major encounters, an-Nuayman remained a light-hearted person who was quick at repartee and who loved to play practical jokes on others.

He belonged to the Banu an-Najjar of Madinah and he was among the early Muslims of the city. He was one of those who pledged allegiance to the Prophet at the Second Pledge of Aqabah. He established links with the Quraysh when he married the sister of Abdur Rahman ibn Awl and later Umm Kulthum the daughter of Uqbah ibn Mu'ayt. She had obtained a divorce from her husband az-Zubayr ibn al-Awwam on account of his harshness and severity.

Unfortunately for a time an-Nuayman became addicted to alcohol. He was caught drinking and the Prophet had him flogged. He was caught a second time and then he had him flogged again. Because he still did not give up the habit, the Prophet ordered that he be flogged with shoes. When all this did not persuade him to stop drinking, the Prophet finally said: "If he goes back (to drinking) then kill him."

This was a severe Pronouncement and Umayr, one of the companions of the Prophet, understood from it that should he return to the drinking of alcohol, an-Nuayman would go outside the pale of Islam and deserve death. Umayr gave vent to his anger and disgust by saying: "La 'nat Allah alayhi - may God's curse be on him."

The Prophet heard Umayr's imprecation and said: "No, no, don't do (such a thing). Indeed he loves God and His Apostle. The major sin (as this) does not put one outside the community and the mercy of God is close to the believers."

While being firm, the Prophet still held out hope for an-Nuayman's reform especially on account of his past sacrifices as a veteran of Badr. Because he was not someone who went out of his way to conceal his actions, it was easier for him to acknowledge his crimes and repent and seek forgiveness from God. This he did and he won the favor of the Prophet and his companions who enjoyed his pleasantries and his infectious laughter.

Once an-Nuayman went to the suq and saw some food being sold which appeared to be tasty and delightful. He ordered some and sent it to the Prophet as if it were a gift from him. The Prophet was delighted with the food and he and his family ate of it. The vendor of the food then came to an-Nuayman to collect the price of it and an-Nuayman said to him: "Go to the Messenger of God it was for him. He and his family ate it."

The vendor went to the Prophet who in turn asked an-Nuayman: "Didn't you give it to me?" "Yes," said an-Nuayman. "I thought you would like it and I wanted you to eat some of it so I had it presented to you. But I don't have any dirhams to pay the vendor for it. So, pay, O Messenger of God!"

The Prophet had a good laugh and so did his companions. The laugh was at his expense, literally, for he had to pay the price of the unsolicited gift. An-Nuayman felt that two benefits came out of the incident: the Prophet and his family ate food that they enjoyed and the Muslims had a good laugh.

Once Abu Bakr and some companions went on a trading expedition to Busra. Various people on the trip were given fixed duties. Suwaybit ibn Harmalah was made responsible for food and provisions. An-Nuayman was one of the group and on the way he became hungry and asked Suwaybit for some food. Suwaybit refused and an-Nuayman said to him:

"Do you know what I would yet do with you?" and went on to warn and threaten him but still Suwaybit refused. An-Nuayman then went to a group of Arabs in the suq and said to them: "Would you like to have a strong and sturdy slave whom I can sell to you." They said yes and an-Nuayman went on: "He has got a ready tongue and is very articulate. He would resist you and say: 'I am free.' But don't listen to him"

The men paid the price of the slave - ten qala'is (pieces of gold) and an-Nuayman accepted it and appeared to complete the transaction with business-like efficiency. The buyers accompanied him to fetch theft purchase. Pointing to Suwaybit, he said: "This is the slave whom I sold to you."

The men took hold of Suwaybit and he shouted for dear life and freedom. "I am free. I am Suwaybit ibn Harmalah..."

But they paid no attention to him and dragged him off by the neck as they would have done with any slave.

All the while, an-Nuayman did not laugh or batter an eyelid. He remained completely calm and serious while Suwaybit continued to protest bitterly. Suwaybit's fellow travellers, realizing what was happening, rushed to fetch Abu Bakr, the leader of the caravan, who came running as fast as he could. He explained to the purchasers what had happened and so they released Suwaybit and had their money returned. Abu Bakr then laughed heartily and so did Suwaybit and an-Nuayman. Back in Madinah, when the episode was recounted to the Prophet and his companions, they all laughed even more.

A man once came to the Prophet on a delegation and tethered his camel at the door of the Masjid. The Sahabah noticed that the camel had a large fat hump and their appetite for succulent tasty meat was stimulated. They turned to Nuayman and asked: "Would you deal with this camel?"

An-Nuayman understood what they meant. He got up and slaughtered the camel. The nomad Arab came out and realized what had happened when he saw people grilling, sharing out and eating meat. He shouted in distress: "Waa 'aqraah! Waa Naqataah! (O my camel!)"

The Prophet heard the commotion and came out. He learnt from the Sahabah what had happened and began searching for an-Nuayman but did not find him. Afraid of being blamed and punished, an-Nuayman had fled. The Prophet then followed his footprints. These led to a garden belonging to Danbaah the daughter of az-Zubayr, a cousin of the Prophet. He asked the companions where an-Nuayman was. Pointing to a nearby ditch, they said loudly so as not to alert an-Nuayman: "We haven't found him, O Messenger of God."

An-Nuayman was found in the ditch covered with palm branches and leaves and emerged with dirt on his head, beard and face. He stood in the presence of the Prophet who took him by the head and dusted the dirt from his face while he chuckled with laughter. The companions joined in the mirth. The Prophet paid the price of the camel to its owner and they all joined in the feast.

The Prophet obviously regarded an-Nuayman's pranks for what they were light-hearted sallies that were meant to create some relief and laughter. The religion of Islam does not require people to disdain seemly laughter and levity and remain perpetually gloomy. An appropriate sense of humor is often a saving grace.

An-Nuayman lived on after the Prophet and continued to enjoy the affection of Muslims. But did he put an end to his laughter? During the caliphate of Uthman, a group of Sahabah were sitting in the Masjid. They saw Makhramah ibn Nawfal, an old man who was about one hundred and fifteen years old and obviously rather senile. He was related to the sister of Abdur-Rahman ibn Awl, who was a wife of an-Nuayman.

Makhramah was blind. He was so weak that he could hardly move from his place in the Masjid. He got up to urinate and might have done so in the Masjid. But the companions shouted at him to prevent him from doing so.. An-Nuayman got up and went to take him to another place, as he was instructed. What is this other place that an-Nuayman took him to? In fact he took him only a short distance away from where he was sitting at first and sat him down.
The place was still in the Masjid!

People shouted at Makhramah and made him get up again all in a frenzy. The poor old man was distressed and said: "Who has done this?" "An-Nuayman ibn Amr," he was told.
The old man swore and announced that he would bash an-Nuayman on the head with his stick if he should meet him.

An-Nuayman left and returned. He was up to some prank of his again. He saw Uthman ibn Affan, the Amir al-Muminim, performing Salat in the Masjid. Uthman was never distracted when he stood for Prayer. An-Nuayman also saw Makhramah. He went up to him and in a changed voice said: "Do you want to get at an-Nuayman?"

The old man remembered what an-Nuayman had done. He remembered his vow and shouted: "Yes, where is he?" An-Nuayman took him by the hand and led him to the place where the Khalifah Uthman stood and said to him: "Here he is!"

The old man raised his staff and bashed the head of Uthman. Blood flowed and the people shouted: "It's the Amir al-Muminin!"

The dragged Makhramah away and some people set out to get an-Nuayman but Uthman restrained them and asked them to leave him alone. In spite of the blows he had suffered, he was still able to laugh at the deeds of an-Nuayman.

An-Nuayman lived up to the time of Muawiyah when fitnah saddened him and discord filled him with anguish. He lost his levity and laughed no more.