There are only three popes given the title Great (as opposed to too many kings): Leo I and Nicholas I. There will be more on them when their feast days roll around.
Gregory's greatness resided in two qualities which were at odds -- extraordinary competence in the face of crisis and a humble, sincere desire to withdraw from the limelight. First, the competence.
Although Rome's goose was overcooked by the time Gregory was born (AD 540), there was still a significant city there. The last emperor had quit sixty-four years prior, leaving Italy nominally in the hands of the Eastern Emperor but practically speaking at the mercy of the marauding armies. Greg's family was tremendously wealthy and he had all the privileges of his class, rising to the post of Praefectus Urbanis (Chief City Administrator) by the time he was thirty. For five years, he managed it brilliantly under the pressure of crumbling infrastructure, plague, flood, famine, and barbarian siege.
The death of his father redirected the course of his life. He gave his vast landholdings to the Church, established monasteries, and entered one as a monk. There, he put himself through such rigorous austerity that he damaged his health. I don't know if it was that damage or just a lifetime of austere living that gave him gout and gastritis, but it probably didn't help.
He was six years there when the Pope called him out to be one of the seven deacons of Rome, awarding him the rank of cardinal. I don't know that he objected to the post, but it wouldn't have mattered since monks take vows of obedience. The next pope sent him to Constantinople to get some military relief from the invading Lombards.
Greg spent six years in Constantinople, learning much about the Eastern Church and making the case for helping Rome. In the former endeavor, he was very successful. In the latter, not so much. When he returned to Rome, he returned to the monastery as abbot and threw himself into relief work, as there had been more flooding, resulting in more starving and more plaguing.
When things settled back to the normal level of Middle Ages misery, he made a plan to gather some monks and go convert the English. Britain, formerly Christian territory, had been conquered by the Angles, Saxons, and Jutes -- Germans, all. Now that they were pagans, it was legal to sell them in slavery if you caught them. Gregory was near the Roman slave market one day when he saw strikingly beautiful blond children being auctioned off. He asked where they were from and was told they were Angles. He made the famous quip that they were "non Angli sed Angeli," i.e. not Angles but Angels. And then he resolved to bring God's word to them.
The plan was altered by his election as Pope. This he resisted because there was no authority ordering his to accept it. [I don't know if he actually made that argument or not, but it makes sense to me.] They leaned hard on him to accept, and eventually he did. And he did lots of cool stuff, like sending Augustine of Canterbury to England to convert the pagans, and establishing the Gregorian Sacramentary and Gregorian chants, and writing lots of books and letters, giving us rich theological and historical sources.
But my new favorite Gregorian accomplishment was the peace with the Lombards. I don't know the terms of the treaty (probably not very good), but I admire the spirit. They had been waging war on Rome for years and the Eastern Emperor was doing nothing. He had an exarch (official representative) in Ravenna, Italy, but the word Byzantine has two meanings: it refers to the Eastern Roman Empire, but it is also a quick was of saying unnavigable, incomprehensibly tangled bureaucracy. As a cardinal, Greg had learned about the Byzantine government and tried to work with it. As Pope, he blew it off and settled his own peace treaty.
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