This is not an original title and the last person that I heard use it was a Seventh day Adventist preacher by the name of Carlos Blake, from Chicago, IL. The reason that I find the context of the social interplay with the LORD and His disciples among the 'sinners' so intriguing is that it is the opposite of what the "faith" experience and standards of Christian Living as taught in the churches today. The behavior of Jesus [Yeshua] certainly did upset the religious leaders of His day because He did not conform to their views of tradition, orthodoxy and false piety [hypocrisy].
Proverbs 23: 20
Do not mix [socialize] with winebibbers, or with gluttonous eaters of meat.
Matthew 9: 10
Now it happened, as Jesus [Yeshua] sat at the table in the house that behold, many tax collectors and sinners came and sat down with Him and His disciples.
Matthew 11: 19a
"The Son of Man came eating and drinking, and they say, 'Look, a glutton and a winebibber, a friend of tax collectors and sinners."
Luke 15: 1-2
Then all the tax collectors and the sinners drew near to Him to hear Him. And the Pharisees and scribes complained, saying, "This Man receives sinners and eats with them."
Luke 7: 36-39
Then one of the Pharisees asked Him to eat with him. And He went into the Pharisees house, and sat down to eat. And behold, a woman in the city who was a sinner, when she knew [heard] that Jesus [Yeshua] was at table in the Pharisee's house, brought an alabaster flask of fragrant oil, and stood at His feet behind Him weeping; and she began to wash His feet with her tears, and she wiped them with the hair of her head; and she kissed His feet and anointed them with the fragrant oil. Now when the Pharisee who had invited Him saw this, he spoke to [within] himself, saying, "This Man, if He were a prophet, would know who and what manner of woman this is who is touching Him, for she is a sinner.
Luke 5: 27, 29-32
After these things He went out and saw a tax collector named Levi, sitting at the tax office. And He said to him, "Follow Me." Then Levi gave Him a great feast in his own house. And there were a great number of tax collectors and others [sinners??] who sat down with them. And their scribes and the Pharisees complained [grumbled] against His disciples, saying, "Why do You eat and drink with tax collectors and sinners?" Jesus [Yeshua] answered and said to them, "Those who are well have no need of a physician, but those who are sick. "I have not come to call the righteous but sinners to repentance."
CONCLUSION: Interestingly, the complaint was against the "disciples" this time and not against Jesus [Yeshua], so His followers must have really been getting their 'party' on. So, how is it that a believer can witness about the grace of God and gift of salvation if not in the company of sinners? The message from many of the pulpits in Christendom is to bring the unbelievers to the local congregation or assembly to hear the Word as opposed to taking it to where they are. The Christian is warned about not going to places where alcohol is being served and drunkenness abounds, as well as possibly being exposed to some form of erotic and seductive adult entertainment, because one just might get tempted and be overcome by the allurement and enticement of the flesh in this environment.
Yes, we are instructed to flee evil in all the forms that it may appear in (Cp. 1 Thessalonians 5: 22) but we are also commanded to take the "Good News" to everyone (Cp. Matthew 28: 19-20) and that just might mean for the sake of sharing the 'gospel' and not indulging in some of these things, we might suffer feeling out-of-place and uncomfortable for the moment. Of course, one has to use common sense, which means that one does not enter into situations where there is illegal activity or immoral practices going on for conscience sake and to avoid criminal prosecution.