She subsequently spent almost a decade at RTL Nederland, hosting the first few seasons of TV makelaar (2001–05) about home buying and the Saturday evening show Dancing with the Stars (2005–07).

Her career change followed her questioning of a term which she deemed racially insensitive during talk show De wereld draait door the previous year.

Her speaking out against institutional racism – and especially Sinterklaas's blackfaced companion Zwarte Piet – caused fierce criticism on social media platforms and racist remarks and threats.

[5][9] When she was twenty years old, she was admitted to the show and musical department of the Amsterdam University of the Arts, but she dropped out shortly after the start of the program because of her first pregnancy.

[16] On TMF, Simons presented the show Sylvana's Soul, which helped popularize R&B in the Netherlands and earned her the nickname "Dutch Queen of R&B".

[16][14] She also recorded the single "Get Close To You" with fellow VJs Fabienne de Vries, Bridget Maasland, and Isabelle Brinkman as part of the music group The Magnificent Four.

It reached position sixteen in the Dutch Top 40 and spent five weeks in that chart, but Simons has told that she was unable to sing and was mostly responsible for backing vocals.

[16][14] Simons left TMF in 1999 and joined SBS Broadcasting later that year, presenting Sexquiz on the beach, a new weekly couples quiz involving stripping candidates, starting in September.

At the same time, she co-presented the Monday evening show Met man en macht (With all his power), in which she and two other women interviewed male guests, in early 2002 and the program Je echte leeftijd (Your real age) with John Williams starting in May 2003.

[9][40] It had been announced shortly before the first airing of Dancing with the Stars that Simons would be replaced by Marilou le Grand as host of TV makelaar.

She did continue hosting Char, and she co-hosted the daily RTL 4 program Nederland vertrekt (The Netherlands leaves) with a dozen other presenters in the summer of 2008 about people going on their holiday.

[59][9][60] She permanently left Radio 6 at the start of 2014, while remaining the host of North Sea Jazz Festival coverage and De zwarte lijst on television.

[68] Simons has told that she decided to publicly speak out against institutional racism following a May 2015 incident and the reactions it had brought about, which included fierce criticism on social media:[69] in an episode of De wereld draait door, presenter Martin Šimek used the word zwartjes (darkies) in a discussion about immigrants, causing Simons to question him on his usage of the word.

The Algemeen Dagblad described 2015 as the year in which Simons had become the figurehead of the Dutch black community because of this event and her opposition to Zwarte Piet, whom she had protested at the national arrival of Sinterklaas in Meppel.

[70][71] She joined the left-wing minority rights party DENK on 18 May 2016, and it was simultaneously announced that she would run for member of the House of Representatives in the 2017 general election.

[72] DENK had been founded the year before by Turkish-born Dutch politicians Tunahan Kuzu and Selçuk Öztürk after they had left the Labour Party (Partij van de Arbeid, PvdA).

[73] Her announcement caused an avalanche of negative reactions on social media platforms, some of which referred to her Surinamese heritage and have been characterized as sexist or racist.

This last category includes a Facebook event, which received tens of thousands of reactions, to wave Simons goodbye on Saint Nicholas Day – a reference to her opposition to Zwarte Piet.

[80] It combined the carnival song Oh Sylvana, the lyrics of which ask her to leave the country, by Rob van Daal with a picture of lynched African Americans, whose faces had been replaced by the one of Simons.

[81] 22 people were prosecuted in April 2017 for threats and insults including the creator of the video, leading to at least twenty of them receiving fines of up to €450 and community-service orders of up to 80 hours.

She founded her new party, which was named after the constitution's article addressing equality before the law and prohibiting discrimination, with DENK's campaign manager Ian van der Kooye.

[90] Simons also co-wrote a book ahead of the election called Artikel 1: Een nieuwe politiek van gelijkwaardigheid (Article 1: A new politics of equality).

Councilor Nicole Temmink (SP) said it would have been better to await the results of an investigation by the Rijksrecherche and Simons's comments were denounced by the rest of the council as well as by Mayor Femke Halsema.

[101] Simons also introduced motions to stop the municipality from fining homeless people for sleeping in the streets and to provide white privilege training for civil servants.

[104] She was awarded the Ribbius Peletier medal in 2021 by the province of North Holland for "being an example to the next generation of women" and for "publicly speaking out against a combination of sexism and racism".

[109] Her election occurred amidst the anti-racism movement Black Lives Matter gaining traction following the murder of George Floyd in the United States by a police officer in May 2020.

[111][112] In the House, Simons has criticized the cabinet's strategy to fight the COVID-19 pandemic, saying that stricter measures such as longer and more stringent lockdowns were required to contain the virus.

[116][117] Simons was less active in debates during the last period of her term due to her membership of the Parliamentary Inquiry into Fraud Policy and Public Service, initiated as a result of the Dutch childcare benefits scandal.

[129][130] Another book by Simons and her half-brother Kenneth Leeuwin, a karate world champion, called In balans about the balance between physical and mental health was published a year later in 2005.

[135] While a member of parliament, Simons disclosed that she had been suffering from chronic pain for ten years, possibly resulting from osteoarthritis, as well as from long COVID since March 2022.