In this world pop culture is often afforded too much weight. The people who are revered as "first" are typically what society deems the "elite" - the rich, famous, and powerful. The Sir Marmaduke San Pelligrinos get the last laugh, while the poor are looked down upon and seen as somehow lesser, as "last". In the Kingdom of Heaven it's the opposite. In Matthew 20:16 Jesus reveals: "so the last shall be first, and the first last."
In Matthew 19:16-30 Jesus meets with a wealthy young ruler who finds himself unable to relinquish his earthly wealth to become a follower of Jesus. But Jesus promised his disciples eternal life, and a hundred times more for the sacrifices they have made. I remember reading this passage when I was much younger and thinking it literally meant that to be a follower of Jesus one had to live in destitution and wear only a burlap sack. But that was lil' me taking the Bible too literally. Living in poverty in the world is not the way to heaven. Salvation is not based on financial status, works, or sacrifice, it is by grace through faith.
This verse also does not imply that this is law in the Kingdom of Heaven. Regardless of wealth and prestige sometimes they are inverse in heaven, but not always. The basis for the ranking is explained in 1 Corinthians 13:3- "If I give all I possess to the poor and give over my body to hardship that I may boast, but do not have love, I gain nothing." It's not the sacrifice, but the love we have for Christ. We are weighed by our hearts and nothing else, the true measure of our faith.
The true message in this verse is that what we find value in on earth is different from the values of the heavenly realm. It's not asked that we sacrifice all of our material assets to be a follower of Christ, just that we stay mindful of worldly thinking. We are all equal in the eyes of God regardless of our current lot in life. When it comes down to it we are only as good as our hearts, and our faith.