I have done this throughout my life, to one extent or another, and mostly, I must admit, in either the wrong spirit or without love and anointing. Only God knows the fruit of it, and I remember the days when I hated God, and heard someone preaching in open air.
It was like someone had a smoky fire pressing my torso; very uncomfortable, to say the least. This was the conviction of sin upon me, though I knew it not; I just knew that this guy was making me sick.
I remember the same feeling encountering a street preacher, when I was filled with pride, and maybe a little ashamed of such a radical approach. "Can't we just all get along?" type of Christianity.
I think I have grown some, but I must say that all of street preaching is not necessarily Spiritual in itself. We can preach from pride, and righteous controversy, and applaud ourselves as the ones going the extra mile for Christ! Most of street preaching is in this vein, as I see it, and the current condemnation preaching that backs a sinner into the Law condemning him to Hell through his own confession is the same; carnal and not spiritual.
Saying this, God can use anything, and there is a power in the Word that goes on in the Universe that God may use later in any individual. I am guilty of doing these same things, so I go lightly, but identify it as I see it. I have had my days street preaching before.
I found a large rock, about ten-twelve feet high. I was in the midst of a huge slum built on the beach shores around Madras, India. I had an interpreter beside me, a PhD. Theologian, who was committed to interpret exactly and whatever I preached. I opened my mouth about Jesus being God, the one and same and only God that created all, and went from there to the Cross , and His sacrifice, and the Holy spirit He gave to men.
After I preached a bit, [ with hecklers!...who I rebuked and confronted...] I asked the crowd gathered who believed my message to raise their hands, and the rest to go on. Often about half of the crowd would stay. I would then tell them that God was going to give them the gift of the Holy Spirit and that they would be born again the second time from above.
I then lined them up, often from 7-8...or more, and approached each one of them, and laid my hands upon them, and ministered to them by name. I watched them become born again, and filled with the Holy Spirit, and cleansed from their sin. It was amazing, and then we turned them over to lay ministers who gathered information from them for follow-up, and gave them bibles, etc.
The Lord had a token for me, a surprise. As nightfall grew, I had to stop, and in my last crowd was a very tall, lanky Indian man, who really got it all, so to speak. He believed my message, and seemed amazingly moved when I laid hands on him for baptism of the Holy One. I spent some time with him, and it became dark, and we had to go.
As we left, I looked over to see these new Christians walk away, and my tall friend was literally glowing...not a little, a lot! He was filled with a visible light akin to a lightbulb, and was smiling as he walked away. I never saw him again.
Sometimes I doubt whether I have ever done any good, but here the Lord wanted me to know, that He touched at least one soul through me, and was happy with both of us.
The strongest exhortation I may submit to anyone desiring to do this, is walk in Love...the God so loved the world kind of thing that opens your eyes to the least of people to see their need as God does, and capture His heart to give them life through His Son.
The second thing is akin to the first. Jesus did preach to crowds. This may or may not be your calling, or forte' in gifting. Remember that Jesus went to the ONE the SINGULAR, over and over...the one leper, the one harlot, the one demoniac....and just loved them.
More souls are one by compassion than hard preaching, I assure you, and one thing you have inside you that the world needs, is that; COMPASSION and MERCY!....and all of us can pray for people...Jesus help Larry...He needs you!..and often, I have see the soul melt with tiny offerings just like this.
"So continuing daily with one accord in the temple, and breaking bread from house to house, they ate their food with gladness and simplicity of heart, praising God and having favor with all the people.
And the Lord added to the church daily those who were being saved."