He has never been afraid to put his reputation on the line by indulging in controversial antics.
But many will be thinking Kanye West has gone too far after he brashly ignored critics and wore a jacket with a Confederate Flag patch in Los Angeles on Saturday.
The Georgia born singer was spotted in the garment after he worked up a sweat in a private boxing lesson.
The green jacket is part of a controversial fashion line he has created which he claims is an attempt to reclaim the Southern Cross from racists.
Kanye, whose father Ray was a Black Panther, has emblazoned his tour merchandise with the flag design, which has been used by extremist groups like the Ku Klux Klan as an emblem.
Explaining his rationale, he said: 'React how you want. Any energy you got is good energy. You know the confederate flag represented slavery in a way -- that's my abstract take on what I know about it.
'So I made the song New Slaves. So I took the Confederate flag and made it my flag. It's my flag now. Now what are you going to do?'
The flag is featured on T-shirts and bags at his new Yeezus tour pop-up shop next door to fiancee Kim Kardashian's clothing boutique in Los Angeles.
The merchandise went on sale at the temporary shop on Melrose Avenue, which he chose to locate right next door to Kim's Dash boutique.
One of the T-shirts features a skull with the flag as the background and the words 'I ain't comin' down,' while another features a skeletal grim reaper wearing the flag as a cloak and carrying a scythe.
Other shirts feature skeletons in various positions, including one kneeling and praying with the words 'Yeezus wants you.' Also on display were shoulder bags bearing the flag.
Kanye's sixth album Yeezus confronts racism head-on, and the items, which were unveiled on the first leg of his tour in Seattle earlier this month, may be a nod to songs such as Black Skinhead and New Slaves.
Kanye, 36, finally spoke out Monday on why he chose to decorate his merchandise with the symbol, which for many is a painful reminder of slavery (although many view it as a symbol of southern pride, and it is still displayed in many areas of the American South).
Kanye is not the only rapper to make reference to the flag in his music, with singers Ludacris, Andre 3000 and Pastor Troy all incorporating the symbol into their album covers or dress.