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In May 2020, Derulo confirmed that after a lengthy negotiation, he had left his record contract with Warner Bros. Records due to creative differences. By leaving the label, Derulo also cancelled the release of 2Sides (Side 2), but confirmed that new music would arrive later in 2020.

"777 was a stage in my life and it has taken a long time to do this album but this name, 2Sides, is more poignant to where I think I am now in my life and what I think the album exudes - the light and the dark side of who I am - the album exemplifies that in both ways. "People have never seen the urban side of what I do as well so they’ll get to see that side for the first time. It's an album that has so many different faces so 2Sides was the more appropriate title."

In a telephone interview with the Official Charts Company, Derulo revealed that he will release "a seven-track EP and then another one shortly after", and that his previous singles "Swalla", "If I'm Lucky", "Tip Toe", and "Goodbye" will not be included on this project because "those songs have had their time. Even though putting them on an album would make it go platinum in two seconds, it’s not about the numbers. These are brand new songs, brand new vibes." Side 1, the first part of 2Sides, was released on November 8, 2019; with Part 2 arriving in 2020. Derulo stars as Rum Tum Tugger in the film Cats, which premiered on December 20, 2019. He will also star as Isley Brothers frontman Ron Isley in the upcoming biographical film Spinning Gold.

"Goodbye", a joint-collaboration with David Guetta and featuring Nicki Minaj and Willy William, was released on August 24, 2018. In 2019, Derulo released the singles "Let's Shut Up & Dance" with Lay Zhang and NCT 127 on February 22, "Mamacita", featuring Farruko, on July 5, and "Too Hot" on August 27.

On February 24, 2017, Derulo released a new single entitled "Swalla", featuring Nicki Minaj and Ty Dolla $ign. On March 17, Pitbull and Derulo released the song "Educate Ya", from the former's album Climate Change. On March 31, Cheyenne Frontier Days announced they added Jason Derulo to their 2017 Frontier Nights concert lineup on Friday, July 28, 2017. At the 2017 Billboard Music Awards on May 21, Derulo announced that his next studio album would be titled 777. "Tip Toe" (featuring French Montana) was released soon after, on November 10. Both songs were expected to be included on the album, according to Derulo. The album was later renamed 2Sides. Derulo explains the reason why he changed the album's name, saying:

On June 29, Derulo announced the release of his first greatest hits album, titled Platinum Hits. Platinum Hits was released on July 29, 2016, with a brand-new song called "Kiss the Sky", which appears on the soundtrack to the film Storks. The album features 11 platinum certified singles.

On September 28, 2016, Derulo guest starred in an episode of the Fox drama Lethal Weapon.

In 2015, Derulo released his single "Want to Want Me" and announced his fourth studio album, Everything Is 4, which was released on June 2, 2015.

On January 22, 2015, Dick Clark Productions announced that Derulo would be a judge in the upcoming 12th season of So You Think You Can Dance, alongside new judge Paula Abdul and returning judge Nigel Lythgoe. "I am truly excited, and eagerly look forward to joining the cast of So You Think You Can Dance," said Derulo. "It is one of the most respected and longest-tenured shows on network television, and I hope to be a part of new growth and continued success."

On March 9, Derulo released the first single from his forthcoming fourth studio album, Everything Is 4, called "Want to Want Me". "Want To Want Me" became the most-added track in the history of Top 40 radio: it was added to 156 monitored pop stations, making it the biggest Top 40 US radio launch thus far. It peaked at number five on the Billboard Hot 100 and topped the UK Singles Chart. The music video for his second single, "Cheyenne", was released on June 30, 2015.

Six months after Derulo's third album Tattoos was released (other than in the U.S) he announced on March 18, 2014 that he would be releasing an album with 4 newly recorded songs and 7 from Tattoos as the U.S album and that it would have different artwork and be re-titled Talk Dirty. Talk Dirty was released on April 15, 2014.

On November 21, 2014, Pitbull released a song off the album Globalization featuring Jason Derulo and Juicy J titled "Drive You Crazy", which was later to become a single on August 21, 2015.

Derulo and singer Jordin Sparks dated for three years, before ending their relationship in September 2014.

In a HitQuarters interview, Rotem highlighted Derulo's dedication to his art by saying, "Jason Derulo has one of the most impressive work ethics I've ever come across – he just keeps knocking out songs in the studio. That's an amazing quality."

On April 16, 2013, Derulo released his single, "The Other Side" to radio on April 23, 2013. As of July 4, 2013 "The Other Side" peaked at No. 18 on the Billboard Hot 100. Derulo announced via Twitter that his third album will be called Tattoos. The album was released on September 24, 2013. The album's second single, "Talk Dirty", was released internationally on July 27, 2013 (digitally). "Talk Dirty" peaked at number three on the Billboard Hot 100.

The album features American hip-hop recording artist 2 Chainz; it is the first single from Derulo to contain a feature. The tracks accompanying music video had already been shot and was released in early August 2013.

"Marry Me" made its US radio premiere on On Air with Ryan Seacrest on August 26, 2013. It was scheduled to be released to all digital retailers as the second single to the U.S. market, third overall, on the same day. On Wednesday December 11, 2013, he was the headline act for Radio City Live in the Echo Arena, Liverpool. He performed Ridin' Solo and Talk Dirty.

On March 28, 2012, Derulo appeared on American Idol to announce he would allow fans to help him finish the lyrics for a new song entitled "Undefeated", as part of a partnership with American Idol and Coca-Cola. Fans were given the opportunity to submit their own lyrics to complete the song, and fans were then given the chance to vote on which lyrics they liked the most. On May 5, 2012, Derulo announced that his first post-neck injury television performance would be on the eleventh-season finale of American Idol, on May 22, 2012. In August 2012, Derulo became a dance master alongside Kelly Rowland, for the first season of the Australian dance talent show Everybody Dance Now. The show was cancelled shortly after its fourth episode aired due to poor ratings.

On July 9, 2012, Derulo announced that he had signed Australian singer-songwriter Arlene Zelina to his record label Future History (co-owned with his manager Frank Harris) after he attended one of her performances at Whisky A Go Go in 2011 before she returned to Melbourne, Australia. On July 10, 2012, Derulo confirmed this on his Twitter.

In 2011, Derulo recorded a track with Demi Lovato titled "Together" for her album Unbroken. His second studio album, Future History, was released on September 27, 2011. Derulo detailed his journey recording the album via a series of webisodes posted on his official website. Its lead single, "Don't Wanna Go Home", was released on May 20, 2011. It landed the number-one spot in the UK and in the top five in Australia. Derulo planned to embark on an eight-date UK tour in support of the album in February 2012, including a show at Wembley Arena on March 1. However, on January 3, 2012, while Derulo was rehearsing for his Future History Tour, he broke one of his vertebrae. As a result, he canceled all of his tour dates.

After producing records for several artists and writing songs for Cash Money Records co-founder Birdman, Young Money Entertainment owner Lil Wayne and rapper Diddy, Derulo signed to minor recording label Beluga Heights. After Beluga Heights became part of the Warner Music Group, Derulo released his debut single "Whatcha Say" in May 2009. It sold over five million digital downloads, gaining an RIAA certification of triple Platinum, and reaching number 1 in the U.S. and New Zealand. Derulo released his second single, "In My Head", in December 2009 and his debut studio album, Jason Derulo, followed on March 2, 2010. He released his second album, Future History, on September 16, 2011; the album was preceded by the release of the UK number-one single "Don't Wanna Go Home". Derulo's third international album, Tattoos, was released on September 24, 2013 and later repackaged as his third U.S. album, Talk Dirty, released on April 15, 2014.

Derulo's debut album, Jason Derulo, stylised with an umlaut as Jason Derülo, was released on March 2, 2010. Jason Derulo first charted within the top ten of the UK and Irish Albums Charts in early March 2010. He spent six weeks promoting the album in his appearances as one of the opening acts for Lady Gaga's 2009–2010 The Monster Ball Tour. The third single of the album is "Ridin' Solo", which was released worldwide on April 26, 2010. By July, the single had reached number nine in the Billboard Hot 100. Derulo has also been featured in a song by new artist Will Roush called "Turn it Up", which also features Stat Quo and Young Buck. He also collaborated with UK singer Pixie Lott on a song titled "Coming Home" from the re-released edition of her album Turn It Up.

On August 4, 2009, Jason released his debut single, "Whatcha Say". It was produced by J.R. Rotem with additional production by Fuego. The track heavily samples the Imogen Heap song "Hide and Seek". In late August 2009, the song debuted at number 54 on the Billboard Hot 100 and hit number 1 in November 2009. It was Derulo's first and only number one hit. The single's music video was released in September 2009; after the single became successful, Derulo began work on his debut album. He released the second single from his album, "In My Head", on December 8, 2009. It debuted at number 63 on the Billboard Hot 100, and reached number five.

Derulo has been writing songs for artists including Diddy, Danity Kane, Donnie Klang, Sean Kingston, Cassie, and Lil Wayne since he was young, also intending on becoming a solo performer. After attending performing arts schools, such as The American Musical and Dramatic Academy, and honing his talents as a singer and dancer, as well as acting in theatre productions like Ragtime and Smokey Joe's Cafe, Derulo won the grand prize on the 2006 season finale of the TV show Showtime at the Apollo. Derulo was discovered by music producer J.R. Rotem, who signed him to his record label Beluga Heights Records and Warner Bros. Records.

Jason Joel Desrouleaux (born September 21, 1989), better known by his stage name Jason Derulo (/d ə ˈ r uː l oʊ / ; formerly stylised as Derülo), is an American singer, songwriter, and dancer. Since the start of his solo recording career in 2009, Derulo has sold over 30 million singles and has achieved eleven Platinum singles, including "Wiggle", "Talk Dirty", "In My Head", and "Whatcha Say".