Stewart hosted a spinoff of The Apprentice in 2005, while Blagojevich appeared as a contestant on Celebrity Apprentice.
Kim met with the President yesterday to ask for a pardon of Alice Johnson, who has been in prison since 1996, serving a life sentence without parole for a non-violent drug offence.
The 69-year-old great-grandmother's offence was her first, and involved relaying phone messages rather than direct involvement with the drugs.
Despite dressing in a conservative black suit to petition the President over the sentencing, Kim was ridiculed for her efforts, with many appalled at the sight of two reality stars wielding such influence.
But the 36-year-old is not one to be silenced by her critics. Her appearance at the White House came after Mr Trump's daughter Ivanka put her in touch with husband Jared Kushner, for whom prison reform is a top priority.
The Keeping Up With The Kardashians star had a series of phone calls with Mr Kushner about the case before the attention-grabbing visit, in which she tried to persuade the President to use his power to free Johnson.
Perhaps remarkably, prison reform is an issue close to Kim's heart, and she has been quietly working on the issue behind the scenes, consulting her own lawyers and funding a new legal team for Johnson.
And it's not a one-off. She is also supporting is the heartbreaking case of Cyntoia Brown, imprisoned at the age of 16 for killing a man who had allegedly drawn her into prostitution and sexually assaulted her.
Brown, from Tennessee, was charged for murder as an adult after she admitted to fatally shooting a 43-year-old she said was using her as a sex slave.
Kim isn't the only celebrity to have spoken out about her case: Cara Delevinge, Snoop Dogg and Rihanna also voiced their outrage after the story recently went viral as Brown returned to court to plead for clemency.
The hashtag #FreeCyntoiaBrown began trending and petitions circulated calling for a presidential pardon, with Kim saying she had called her lawyers to see what could be done.
Brown, 29, was imprisoned in 2004 for 60 years, 51 without parole, after the teenage runaway was allegedly trafficked by a pimp nicknamed "Kut-throat" in Nashville, Tennessee, before killing her buyer.
Brown said that over several days, she was repeatedly drugged, raped by different men at gunpoint and choked until she passed out at the pimp's hotel room.
She was then allegedly purchased by real estate agent Johnny Allen, an ex-soldier, for sex.
He took her to his home, where he had a stash of guns, and allegedly behaved in a threatening manner.
When Allen rolled over as they lay in bed, Brown said thought he was reaching for one of his firearms on the floor, and she shot and killed him with a gun she kept stashed in her handbag.
"Cyntoia's sentence is wholly disproportionate for a 16-year-old girl, and therefore unconstitutional," Marsha Levick, deputy director and chief counsel for the Juvenile Law Center, said in a statement.
Riya Saha Shah, senior supervising lawyer at the Juvenile Law Center, said sentencing practices in Tennessee were "unduly harsh, foreclosing both any realistic opportunity for parole or any individualised consideration."
Republican Governor Haslam has not granted any clemency cases in his tenure.
Kim told Mic, whose social video alerted her to Johnson's case, that the great-grandmother was the first "of many" prisoners she would fight for.
"If you think about a decision that you've made in your life and you get life without the possibility of parole for your first-time, non-violent offence, there's just something so wrong with that," she said.
"In all honesty, how I felt I was like, where I'm at in my life right now, to go and spend my money buying material things just doesn't satisfy me the way that it used to.
"I'm just at a different my place in my life, so I thought, 'Well, if I could put the money into a shopping spree, which sounds ridiculous, to save someone's life, and do that once a year, then that would make me, just my heart fuller.'"
Whatever you think of the Kardashians, sending a reality star to promote important causes with the fame-obsessed President doesn't sound like a terrible idea.
Although husband Kanye West recently revealed his admiration for the President in a string of strange tweets and caused widespread offence, Kim was a vocal supporter of Hillary Clinton.
In response to criticism that she shouldn't engage with Mr Trump, she replied: "I'm just focused on criminal-justice reform and helping one person at a time. And so far, the White House has been really receptive to my calls, and I'm grateful for that. And I'm not going to stop that because people personally don't like Trump."
She noted that social media can be "powerful", allowing young people to learn about issues and speak out on them. "You can just be clicking through and see something that just tugs at your heart and change your life, and change someone else's life."
Mr Kushner has made prison reform a priority after his father served time, and recently pushed through a bill called the First Step Act. It is uncertain, however, whether it will make it through the Senate.
Mr Trump has at times talked tough on criminal punishment, but said he would sign the act and has pardoned prisoners with strong media or celebrity backing, such as late boxer Jack Johnson.
Barack Obama pardoned more than 1700 prisoners locked up for non-violent drug crimes.
