Commercial success (2014–2020)
In 2014, he appeared in a cameo role in Vamsi Paidipally's action thriller film Yevadu, alongside Kajal Aggarwal. Y. Sunita Chowdary of The Hindu, in her review, wrote that "Allu Arjun shows what an actor can do even in a short role, in the few minutes he packs his experience, internalises the character and makes an impressive exit even as he loses his identity." His next film was Surender Reddy's Race Gurram, in which he played Allu Lakshman "Lucky" Prasad, a carefree guy. He joined the production of the film in May 2013. The film was successful at the box office, with the film being Allu's first ₹100 crore grosser. Writing to Deccan Chronicle, Suresh Kavirayani felt that Allu Arjun steals the show with his energetic performance and also praised his dancing skills in the film. Ranjani Rajendra too praised his dance moves, comic acting and performance in the action sequences, but felt that the story is predictable and routine. For his performance, he won his third Filmfare Award for Best Actor – Telugu and was nominated for the SIIMA Award for Best Actor – Telugu for the second time after Julayi. Allu Arjun produced and acted in a short film I Am That Change, which was released in August 2014. The film was directed by Sukumar, to spread awareness on individual social responsibility. Upon its release, the short film received viral response online and was acclaimed by many including celebrities for its concept and execution. It was screened in theaters across Andhra Pradesh and Telangana.
Allu Arjun next appeared in Trivikram Srinivas's S/O Satyamurthy (2015), which was released on 9 April 2015. The film was a commercial success, with critics praising his performance. His performance in the film earned him his seventh nomination for the Filmfare Award for Best Actor – Telugu. Following the film, he next played Gona Ganna Reddy in Guna Sekhar's biographical action film Rudhramadevi (2015). The film based on the life of Rudrama Devi, is the first Indian 3D historical film. He has learned and was seen speaking in the Telangana Telugu, for the character in the film. The Times of India called his performance "impeccable" and "whistle-worthy". Due to the wide response and popularity for the character Gona Ganna Reddy, in 2021 director Guna Sekhar said that he will be directing a film solely based on the character, with Allu Arjun in the lead role, after Shaakuntalam. For Rudhramadevi, he won the Filmfare Award for Best Supporting Actor – Telugu and became the only actor to win both the Filmfare Award for Best Actor – Telugu and the Filmfare Award for Best Supporting Actor – Telugu. He also won three other awards for his performance, including Nandi Award for Best Character Actor.
In 2016, he acted in Sarrainodu, directed by Boyapati Srinu. Although the film received negative reviews for the screenplay and story, it was a major commercial success at the box office, grossing over ₹127.6 crore. Allu Arjun called it as a "landmark film" in his career. His performance in the action scenes and dance numbers was praised. HIs performance in the film won him the Filmfare Critics Award for Best Actor – Telugu, in addition to his eighth nomination for the Filmfare Award for Best Actor – Telugu. The same year, in June, he announced his next film with producer Dil Raju for the third time for DJ: Duvvada Jagannadham. Released in 2017, the film directed by Harish Shankar, in which he played the role of Duvvada Jagannadham "DJ" Shastri, alongside Pooja Hegde, Rao Ramesh and Subbaraju. He appears as a caterer, who is an undercover cop. Firstpost's Hemanth Kumar praised his dance and wrote that "look beyond Allu Arjun's classy moves in Seeti Maar and Asmaika Yoga, all you find is a story that struggles to find its rhythm." India Today too lauded his dance but criticised the film's screenplay and called it "Boring-ah, bore-asya, bore-obiah".
The next year, in May, his film under the direction of writer turned director Vakkantham Vamsi, Naa Peru Surya was released. He played Surya, an Indian Army soldier who has anger management issues. Allu Arjun spent considerable time learning the tricks and stunt sequences from professionals, especially for the dance numbers and action sequences. Upon release, the film received mixed reviews and was successful at the box office. A critic called his performance as Allu Arjun's "career-best" and cited it as the "biggest strength to the film". Vyas of The Hans India stated that "Allu Arjun is supremely talented and has delivered an energetic performance in the movie." Hindustan Times's Priyanka Sundar opined that "Allu Arjun tries to do his best in the shoes of a soldier, but at places we see that it looks forced."
In December 2018, his next project Ala Vaikunthapurramuloo was announced, with Trivikram Srinivas as the director. Pooja Hegde was selected to play the female lead role, thus marking his second collaboration with Hegde after DJ: Duvvada Jagannadham. He joined the production of the film in April 2019. Produced jointly by Allu Aravind and S. Radha Krishna, the film marks the third collaboration of Allu Arjun and Trivikram after Julayi (2012) and S/O Satyamurthy (2015). The film was released in January 2020. Allu Arjun's performance received highly positive reviews. A review posted by Rohit Mohan on Koimoi said that "Be it comedy, action, emotions, style and of course dance, the star actor nails it in the film, as 'Bunny' made to audience groove to his tunes with his act." Film Companion felt that Allu Arjun's performance in the board-room scene was the highlight of the film. Bhavana Sharma of International Business Times, opined that Allu Arjun went into the skin of the character. The film his career's highest grosser and stands among the highest-grossing Telugu films. Allu Arjun's dance performance in the song "Butta Bomma" received wide response.