Smith is hoping to take advantage of the incumbent's apparent political weakness and his own celebrity. The 33-year-old is a rapper and a Grammy Award winning writer.
"We need fresh ideas. We need a new way to lead," said Smith.
Smith captured 26 percent of the ward's vote last month, finishing second to the 46 percent garnered by incumbent Willie Cochran.
Cochran has struggled to revive the economically depressed ward since his 2006 appointment by Mayor Daley after Alderman Arenda Troutman was indicted on federal corruption charges.
"The trust in the ward and the leadership of the ward had to be restored. Two years in took to do that," said Cochran.
"The leadership that we have had thus far has not been effective for the residents of the 20th Ward," said Smith.
Smith has used the n-word and profanity in his lyrics that have at times romanticized so-called thug life. His artistic career has become a campaign issue.
But Smith charged Tuesday that Alderman Cochran has used profanity during the campaign. Cochran denied the allegation and predicts he will be one of the reform-minded runoff candidates to be supported by Mayor-elect Rahm Emanuel.
"I expect the mayor-elect to know that Willie Cochran will be there to work with him," said Cochran.
But Smith says Emanuel should pay closer attention to the voters who he says who have made a decision about Alderman Cochran.
"What we know is that 54 percent of the people voted against the incumbent," said Smith.
Turnout in the 20th Ward was only 38 percent in the February election. Alderman Cochran and Mr. Smith are hoping that more people vote in the April 5th runoff. But without a mayor's race to consider turnout in Chicago runoff elections has always been lower.