Shrila Rupa Goswami has been attributed with the honor of being the person who realized the mano-‘bhistam, the innermost heart’s desire, of Shri Krishna Chaitanya Mahaprabhu. 
Shrila Rupa Goswami has been attributed with the honor of being the person who realized the mano-‘bhistam, the innermost heart’s desire, of Shri Krishna Chaitanya Mahaprabhu. (In the wallpaper: from left to right: Shri Gopinath, ISKCON Chowpatty, Deity of Rupa Goswami, Shri Vrindavan Dham, Shrimati Radharani and Shri Krishna Chaitanya).
Shrila Rupa Goswami, the foremost of the six Goswamis of Vrindavan, was an incarnation of Rupa Manjari, the most important of the eight confidential maidservants of Shrimati Radharani in the eternal spiritual Vrindavan.
It is said that without taking shelter of Shrila Rupa Goswami one cannot enter into the pastimes of Lord Chaitanya, and without taking shelter of Rupa Manjari one cannot enter into the confidential loving pastimes of Shri Shri Radha Krishna.
Shrila Rupa Goswami’s lineage can be traced back to Karnataka, South India where his Saraswata brahmana descendants held influential positions. Shrila Rupa Goswami's nephew, Jiva Goswami has explained in his Laghu Toshani that Rupa's descendants were of the Bharadvaja gotra and were learned in the Yajur Veda.
A brahmana called Sarvajna was seventh in the ascending geneological line of Rupa Goswami and was known by the title 'jagadguru'. He was a king as well as a learned scholar. His son, Aniruddha was also an acclaimed scholar. Aniruddha had two sons, Harihara and Rupeshvara. While Rupeshvara was knowledgable in the Vedic literatures, his brother became expert in weaponry and politics.
When their father died, the kingdom was divided between the two sons. However, Harihara seized Rupeshvara's land by force and forced the family to migrate to Paurastyadesha. Rupeshvara's son, Padmanabha was spiritually and materially very successful. Padmanabha relocated his family to Nabahatta (Naihati) on the banks of the Ganges River. Padmanabha had eighteen daughters and five sons, the youngest son being Mukunda.
In the course of time, Mukunda's son, Kumaradeva, moved to Jessore. His sons were Santosha (Rupa), Amara (Sanatana) and Shrivallabha (Anupama). On the demise of Kumaradeva, the three sons moved to Sakurma, near the capital of Gaudadesha (Bengal) where they continued their studies.
The three brothers studied the Nyaya-shastras (treatise on rhetoric) from the famous logician Vasudeva Sarvabhauma Bhattacharya and his brother Madhusudana Vidyavachaspati. They also studied Sanskrit, Arabic and Persian.
Due to their noble characters and academic proficiency, Rupa and his elder brother Sanatana were later forced into government service by the Sultan of Bengal, Alauddin Hussein Shah (1493-1519) which led to their excommunication from Hindu society by the orthodox caste brahmanas of Gauda. Rupa became the Sultan's chief secretary (dabir khas), while Sanatana became the state revenue minister (sakara mallika).
Rupa and his brothers made their residence at the state capital of Ramakeli and it was here, in 1514, that they met Shri Chaitanya Mahaprabhu for the first time. At that time all three brothers were employed as important ministers in the Mohammedan government of Bengal under Hussain Shah.
Approaching the Lord humbly they prayed to Him to somehow rescue them for their bonded state. Lord Chaitanya assured them that now they had surrendered to Krishna, they would soon be delivered and would be able to join His sankirtana movement. 
Rupa and Anupama immediately decided to go and they wrote a letter to Sanatana telling him of their plans and asking him to join them in Vrindavan. They also told him that they had left 10,000 gold coins in case he was in need of financial help. Later, when Sanatana was thrown into prison by the Sultan for disobedience, he used this money to bribe the jailer and escaped to Varanasi to meet there with Chaitanya Mahaprabhu. (In the image: The jail where Sanatana Goswami was kept, Ram Keli).
After some months both Rupa and Anupama were freed from service. Rupa loaded all his wealth onto two boats and left with his brother Anupama for their ancestral home at Fatiabad in Jessore, where they distributed it. They then sent two messengers to Puri in Orissa to get news of Chaitanya Mahaprabhu's plans. The messengers returned with the news that Mahaprabhu had already left Puri for Vrindavan.
Rupa and Anupama immediately decided to go and they wrote a letter to Sanatana telling him of their plans and asking him to join them in Vrindavan. They also told him that they had left 10,000 gold coins in case he was in need of financial help. Later, when Sanatana was thrown into prison by the Sultan for disobedience, he used this money to bribe the jailer and escaped to Varanasi to meet there with Chaitanya Mahaprabhu.
On his return trip from Vrindavan, Chaitanya stopped at the holy city of Prayaga (Allahabad). It was here that Rupa and Anupama met him for the second time. At the historic Dasasvamedha Ghat, Sri Chaitanya imparted confidential instructions to Rupa Goswami and explained in detail all the fundamental principles of the doctrine of Gaudiya Vaishnavism.
Rupa Goswami was specifically commanded by Chaitanya Mahaprabhu to carry out two tasks: (1) to find and establish the lost ancient and original Deities of Lord Krishna as well as to re-discover and restore the holy places associated with His leela in Vrindavan, and (2) to write and preach Gaudiya Vaishnava theology. He then sent Rupa Goswami to Vrindavan to carry out these tasks.
Rupa Goswami first arrived in Vrindavan along with his elder brother Sanatana Goswami in the year 1516, after receiving the direct order of Lord Chaitanya. Through his writings Shrila Rupa Goswami chalked out the perfect spiritual path for all the followers of Lord Chaitanya down through the ages.
It was Rupa Goswami who more than anyone else, firmly established the sankirtana movement of Lord Chaitanya. He wrote a large number of important books on the science of bhakti-yoga and after the disappearance of Lord Chaitanya in 1534, Rupa became the undisputed leader of all the Gaudiya Vaishnavas in the world.
Even today all Gaudiya Vaishnavas are known as Rupanugas, or followers of Shrila Rupa Goswami.
After spending some time in Vrindavan, Rupa and Anupama left to visit Lord Chaitanya in Puri. It is believed that on this long and arduous journey Anupama left his body. On his way to Puri, Rupa Goswami started to write a drama about Lord Krishna's pastimes in Vrindavan and Dwaraka.
On arrival at a village named Satyabhamapur in Orissa, he had a dream wherein a beautiful woman appeared before him and asked him to write a separate drama about her. When Rupa awoke the next morning he realized that she was Lord Krishna's most possessive queen, Satyabhama, and decided to write a separate drama about the Lord’s Dwaraka leela.
On Rupa's arrival at Jagganatha Puri, he met Lord Chaitanya and showed the Lord the outline of his two dramas. The Lord confirmed that writing two dramas mixing the lilas of Vrindavan and Dwaraka was not proper as their was a vast difference between them. In Vrindavan the Lord enjoys the parakiya-rasa, where as in Dwaraka He enjoys the Swakiya-rasa.
Lord Chaitanya as well as Ramananda Rai were delighted to read the early drafts of these two dramas, which were eventually called Vidagdha Madhava and Lalita Madhava respectively. These two works are considered by Gaudiya Vaishnavas to be the most important dramatic literatures in the Sanskrit language.
Rupa Goswami stayed ten months in Puri and received further instructions on devotional service from Lord Chaitanya. The Lord then asked Rupa to return to Vrindavan and complete the task of rediscovering the lost holy places of Lord Krishna's pastimes.
On returning to Vrindavan, Rupa Goswami discovered at Brahma Kunda the Deity of Vrinda Devi, from who the town of Vrindavan gets its name, this Deity was later moved to Kamyavana. Rupa Goswami then discovered the famous Govindev ji Deity and immediately established Lord Govindaji's worship on a grand scale.
On hearing the good news of Rupa's progress, Lord Chaitanya sent some of his best men to assist Rupa in serving the Deity of Govindaji and establishing the Lord's mission in Vrindavan.
Shortly Rupa and Sanatana Goswamis were joined by Ragunatha dasa Goswami, Gopal Bhatta Goswami, Raghunatha Bhatta Goswami and Shrila Jiva Goswami. These great personalities become famous as the six Goswamis of Vrindavan. Jiva Goswami, who was the son of Rupa's brother Anupama, became the most important disciple of Rupa Goswami.
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On returning to Vrindavan, Rupa Goswami discovered at Brahma Kunda the Deity of Vrinda Devi, from who the town of Vrindavan gets its name, this Deity was later moved to Kamyavana. (In the wallpaper: A tree in Vrindavan Dham, Shrimati Vrinda Devi, Kamyavan).