The Sahaabah RadhiAllaahu Anhum too would easily cry, following in the footsteps of Rasulullaah SallAllaahu Alayhi Wasallam.

1.) Anas RadhiAllaahu Anhu narrates, “Rasulullaah SallAllaahu Alayhi Wasallam delivered a sermon to us. I never heard a sermon like it. He  said, ‘If you only knew what I know, you will laugh little and cry a lot.’ On hearing this, the Sahaabah RadhiAllaahu Anhum covered their faces and began weeping.” (Bukhaari no.4621, Muslim no. 901)

2.) Anas RadhiAllaahu Anhu narrates that Rasulullaah SallAllaahu Alayhi Wasallam said to Ubayy ibn Ka‘b RadhiAllaahu Anhu, “Allaah Jalla Jalaalahoo ordered me to recite [Surah] Lam yakunilladhina… to you.”
He [Ubayy RadhiAllaahu Anhu] asked, “Did Allaah Jalla Jalaalahoo mention me by my name?”
He  replied in the affirmative. On hearing this, Ubayy RadhiAllaahu Anhu began crying. (Bukhaari no. 3809, Muslim no. 799) 

Mulla Ali Qaari Rahimahullaah states that these tears were either due to joy and happiness that Allaah Jalla Jalaalahoo had mentioned his name; or it was due to fear that he was unable to fulfil the gratitude of this great bounty. The reason why he was singled out for this bounty is that he had undergone great sacrifices in reaching a level of perfection in memorization of the Quraan and Tajweed so much so that Rasulullaah SallAllaahu Alayhi Wasallam said regarding him أقرأكم أبي “The greatest Qaari (reciter) amongst you is Ubayy.”
Allaah Jalla Jalaalahoo wanted to teach the Muslim Ummah that people should learn from him the manner of tilaawah, just as Rasulullaah SallAllaahu Alayhi Wasallam had learnt from Jibreel Alayhis Salaam. In this way, the later generations would learn from the preceding generation. Thus, many Tabi’in learnt the manner of recital from Ubayy RadhiAllaahu Anhu. (Mirqaat vol. 5 page 6)

3.) Anas RadhiAllaahu Anhu narrates that after the demise of Rasulullaah SallAllaahu Alayhi Wasallam, Abu Bakr RadhiAllaahu Anhu said to Umar RadhiAllaahu Anhu, “Come, let us go and visit Umm Ayman RadhiAllaahu Anha as was the habit of Rasulullaah SallAllaahu Alayhi Wasallam to visit her.”
When they went to her, she began crying. They asked her, “Why are you crying? Don’t you know that Rasulullaah SallAllaahu Alayhi Wasallam has a better place with Allaah Jalla Jalaalahoo?”
She replied, “I am not crying because I do not know that Rasulullaah SallAllaahu Alayhi Wasallam has a better place with Allaah Jalla Jalaalahoo. Rather, I am crying because divine revelation has now come to an end.”
This statement of hers prompted them to cry as well. And they began crying with her. (Muslim no. 2454)

4.) Ibn Umar RadhiAllaahu Anhu narrates, “When the illness of Rasulullaah SallAllaahu Alayhi Wasallam became severe, he was asked as to who should lead the salaah. He replied, ‘Order Abu Bakr to lead the people in salaah.’
Aaishah RadhiAllaahu Anha said, ‘Abu Bakr is a very soft person. When he recites the Quraan, he is overtaken by crying.’
Rasulullaah SallAllaahu Alayhi Wasallam said, ‘Order him to lead the salaah.’”

Another narration from Aaishah RadhiAllaahu Anha states that she said, “When Abu Bakr stands in your place, he will not be able to make the people hear his recitation of the Quraan because of his crying.” (Bukhaari no. 664, Muslim no. 420)

5.) Irbaad ibn Saariyah RadhiAllaahu Anhu narrates, “Rasulullaah SallAllaahu Alayhi Wasallam delivered a very comprehensive lecture to us. Our hearts trembled by it and our eyes shed tears.” (Ibn Majah no. 42)

In actual fact, Rasulullaah SallAllaahu Alayhi Wasallam and the Sahaabah RadhiAllaahu Anhum encouraged us to cry. Sa’d Ibn Abi Waqqas RadhiAllaahu Anhu narrates that Rasulullaah SallAllaahu Alayhi Wasallam said,

ابْكُوا، فَإِنْ لَمْ تَبْكُوا فَتَبَاكَوْا

 “Cry (in the love of Allaah Jalla Jalaalahoo or due to His fear). If you cannot cry, then imitate the form of those who cry.” (Ibn Majah no. 4196)

Ibn Abi Mulaikah Rahimahullaah said, “We sat by Abdullah ibn Umar RadhiAllaahu Anhu at Hijr (place where people were punished when they refused to believe in their nabi). He said,

ابْكُوا فَإِنْ لَمْ تَجِدُوا بُكَاءً فَتَبَاكَوْا، لَوْ تَعْلَمُونَ الْعِلْمَ لَصَلَّى أَحَدُكُمْ حَتَّى يَنْكَسِرَ ظَهْرُهُ وَلَبَكَى حَتَّى يَنْقَطِعَ صَوْتُهُ

“Cry. If you are unable to cry, then imitate the one who cries. If any of you had true knowledge, then you would have performed salaah until your back broke, and you would have cried until your voices terminated.” (Mustadrak of Haakim no. 8723)

Explanation: Since crying is not a volitional action, therefore Rasulullaah SallAllaahu Alayhi Wasallam advised his followers to imitate the form of those who cry to draw the mercy of Allaah Jalla Jalaalahoo since this is within the control of every person. Such a person will also not be deprived of Allaah Jalla Jalaalahoo’s mercy.

To be continued In Sha Allaah.

مَوْلَاىَ صَلِّ وَ سَلِّمْ دَائِمًا أَبَداً عَلىٰ حَبِيْبِكَ خَيْرِ الْخَلْقِ كُلِّهِمِ