1990s

Upon his return to Trinidad and Tobago, Ramesar was employed by the Government Information Service as a director/producer. It was during this decade that most of his seminal shorts on the culture of Trinidad and Tobago were made. The earliest of his shorts was Mami Wata (1992), the first on-screen depiction of an Orisha feast for the goddess Oshun. He went on to do a film series of interviews with the pioneers of the steelband movement, which includes Pan: The Overture (1993) and Pan under the Sapodilla Tree (1994). .

His work includes shorts on traditional Carnival figures and players (Minstrel Lady, 1998; Robber Talk, 1998; Black Indian, 1998; Fire Dance, 1998; Masquerade, 1998), East Indian culture (Jahaaji Mai, 1995; Children of Fatel Razack, 1998; Journey to Ganga Mai, 1999) and Tobago culture (A Wedding in Moriah, 1997). His work in the short film form also covered many other themes such as cricket (Spinner's Wicket, 1998), parang (Spanish Time, 1998) and more contemporary subjects such as the cottage industries created by people living near a garbage dump in Arima (Picking Up the Pieces, 1999).

2000s

Ramesar was the featured filmmaker at Carifesta VII in St. Kitts & Nevis (2000). Additionally, he filmed Trinidad and Tobago's cultural participation at Carifesta VIII in Suriname (2003) and chaired the Carifesta Film Committee in Trinidad and Tobago (2006).

In 2001, Ramesar participated in the Big River International Artists' Workshop and Exhibition. The following year, he directed the filming of the acclaimed musical Carnival Messiah in the United Kingdom. His work was featured in the first National Sculpture Exhibition, and at the first Kairi film Festival, in Trinidad in 2003.

In 2002 and 2003, Ramesar took part in the inaugural and second editions of the Festival of African and Caribbean Film (Barbados), where he delivered a public lecture and screened films; Caribbean Input screening in Jamaica; the Zanzibar International Film Festival (Republic of Tanzania); Cine Latino Film Festival (San Francisco); Sin Fronteras, University of Wisconsin, Madison, where he conducted a week-long workshop on Caribbean film; and Swimming Against the Tides, Caribbean Culture in the Age of Globalization, Bowdoin College, Maine, where he lectured and screened films. His work was also featured at the VideoBrasil Festival, São Paulo, in 2003.

In 2006, Ramesar's fantasy drama SistaGod – which he directed, wrote and produced – premiered at the Toronto International Film Festival and was subsequently screened at the Trinidad and Tobago Film Festival.^[1] The first chapter of a film trilogy, it tells the story of the coming of a black female messiah (played by Evelyn Caesar Munroe) during a period known as the "Apocalypso". The movie integrated traditional Trinbagonian Carnival characters and a powerful female lead into its narrative, whilst tackling issues such as westernization, spiritualism and culture. Sistagod remains the sole Trinidad and Tobago feature film to gain official selection at a major international film festival.

In 2007, Ramesar served as the first filmmaker in residence at the University of the West Indies. Film theory on the UWI film Programme was introduced in 2006 by the co designers of the BA in Film, Dr Jean Antoine-Dunne, who taught film theory and aesthetics and Dr Bruce Paddington. Ramesar wrote, produced and directed Her Second Coming in 2009. The second chapter of his SistaGod trilogy, Her Second Coming centers on SistaGod (played in this movie by real-life albino actress/singer Crystal Felix^[2]) and her progeny battling for survival in a post-apocalyptic world devoid of human life. The film made its world premiere at the Trinidad and Tobago Film Festival in the same year.

In 2009, Ramesar co-founded the Caribbean Travelling Film School, which aims to incubate filmmaking talent throughout the Caribbean region. This is, in part, a continuum of a blueprint he developed in the 1980s for the consolidation of a regional cinema, which would involve filmmakers traveling in Caribbean communities and fostering a citizens' cinema, which he termed "The Moving Image".

2010s

In 2010, Ramesar worked on his yet-to-be-released third feature film, Stranger in Paradise, which involved a Chinese woman arriving in Barbados speaking only Mandarin. In 2014, Ramesar flew to South Africa to begin work on his next feature film, Shade, which centred on a young albino woman (Mathapelo Ditshego) from Soshanguve, South Africa, with dreams of becoming an R&B singer.^[3]

Ramesar's next feature film, Haiti Bride, released in 2014, is the story of a Haitian-born woman who returns to her homeland to meet her husband who lost his memory after the 2010 Haiti earthquake. Shot entirely on location in Haiti, it was the first African diaspora / Caribbean feature film selected in the 2015 feature film competition at the Pan African Film & Television Festival, Africa's largest and oldest film festival, in Ouagadougou, Burkina Faso. Ramesar was the first Caribbean filmmaker in the festival's history to compete for the prestigious Etalon de Yennenga award.

Between the months of July to August 2015, he visited India, specifically Mumbai, Delhi, Agra and Goa, where he continued fostering partnerships with film schools, as well as researching film education and production infrastructures. He met and held discussions with the heads of film schools in Delhi – namely Jamia Millia (Central University), Delhi, and the Asian Academy of Media Studies Film School at Filmcity, New Delhi – towards establishing a relationship between their respective institutions, along with seeking co-production, undergraduate exchange and post-graduate opportunities for the film students of University of the West Indies (St. Augustine Campus).

In December 2015, he screened Haiti Bride at both the 2015 edition of the Ghetto Biennale, a cross-cultural arts festival held in Port-au-Prince, Haiti,^[4] and in the commune of Jacmel, where most of the film was shot.

Short films

• 1985 – American Dream
• 1986 – Grey
• 1987 – Going Up
• 1987 – Confessions of Brother Man
• 1988 – Going Up
• 1989 – Rum & Coke
• 1990 – Bhava Tanha
• 1991 – Blue Eyes
• 1992 – Mami Wata
• 1992 – Clear D' Way
• 1993 – Pan: The Overture
• 1994 – Pan Under the Sapodilla Tree
• 1995 – The Kindest Cut
• 1995 – Strings & Steel
• 1995 – Caribbeing
• 1995 – Songs Across the Rainbow Bridge
• 1995 – Jahaaji Mai
• 1996 – Mayaro: The Drum, The Bois & The Moon
• 1996 – Testament
• 1996 – Re-Generation
• 1996 – Parlour People
• 1997 – Joe Polle's Scarborough Sax
• 1997 – A Wedding in Moriah
• 1997 – Mr. Washington's Place in History
• 1997 – Destiny: Live from Black Rock
• 1998 – Children of Fatel Razack
• 1998 – Minstrel Lady
• 1998 – Robber Talk
• 1998 – Black Indian
• 1998 – Fire Dance
• 1998 – Masquerade
• 1998 – Batman
• 1998 – Doubles: Bara Part 1 & Bara Part 2
• 1998 – Boat a' Dem
• 1998 – Spinner's Wicket
• 1998 – Spanish Time
• 1998 – Chinese Medicine
• 1998 – Original People
• 1998 – First People
• 1998 – A Man of the People
• 1999 – Olokun: Lord & Mistress of the Deep
• 1999 – I, Marcus Garvey
• 1999 – Dancing in the Light
• 1999 – Body Language
• 1999 – Stepsisters
• 1999 – Longdenville Diva
• 1999 – Foundation
• 1999 – Spirits Rising
• 1999 – Picking up the Pieces
• 1999 – Journey to Ganga Mai
• 2000 – Celebration
• 2000 – Man of Steel
• 2001 – Coronation
• 2001 – The Saddhu of Couva
• 2001 – B.C. (Before Columbus)
• 2002 – Awake
• 2002 – Bois
• 2003 – In My Skin
• 2003 – A Brief History of Queen's Hall
• 2003 – Tobago to Africa & Back
• 2003 – Jackie Hinkson: The Work of Art
• 2003 – An Animated Conversation with Camille Selvon
• 2003 – Super Moxi Patu
• 2003 – Canboulay
• 2004 – The A.B.C's of Traditional Mas
• 2004 – Carnival Messiah

Feature-length films

• 2006 – SistaGod
• 2009 – SistaGod II: Her Second Coming
• 2010 – Stranger in Paradise
• 2014 – Shade
• 2014 – Haiti Bride