Elections were held on 3 March 1996, with the results ushering in the conservative government of José Maria Aznar. He and Partido Popular would stay in power until March 2004. This change in government did not bring any fundamental changes to Pride in Madrid, with many of the initial trends in the period having already been started in the Felipe González era.
The commercialization and involvement of businesspeople in the production of Pride and Pride adjacent activities began to take place more rapidly at the end of the 1990s, with the formation of Asociación de Empresas y Profesionales para gays y lesbianas de Madrid y su Comunidad (AEGAL) in Chueca. One of the people who was involved with the group early on was lesbian bar owner Desiré Chacón Ríos, who was the contact for the group with COGAM and FELGT. Her involvement with AEGAL would soon see her more involved with Pride management. 
Día del Orgullo de Gays, Lesbianas y Transexuales, the official name for Pride in 1996, convened once again by COGAM followed the same route as the previous year from Puerta de Alcalá to Puerta del Sol and continued to take place on a weekend, with an attendance between one, two or three thousand people on a day with 30 C / 86 F degree temperatures. The motto, chosen by a group of fifty volunteers, was “Visibles”, and had begun to take on a distinctly Anglo-Saxon commercialized flavor. This would be one of the last marches where the pink triangle as a separate symbol representing the fight for homosexual rights would be used. Political demands made during the march included one for same-sex marriage and access to an AIDS inhibitor treatment being used in other countries be distributed in Spain. The political aspects of Madrid Pride began to be overshadowed at this march by the commercialization and party like atmosphere, a process that continued to accelerate in the following years in the media.
Pedro González Zerolo, president of COGAM said of Pride that year, “Being gay is not enough,” and going on to say, “We want to ask for lost rights for all, more citizen participation now that political power has moved away from the street and, also, more Luddism in these times of farce.”
Lesbians were visible participants, with a few lesbian and mixed groups taking part including LSD, Feminista de Lesbianas, and COGAM. A lesbian orchestra led the march, followed behind by the parade’s first float and first commercially sponsored float featuring Alaska, the Spanish-Mexican singer whose real name is Olvido Gara Jova, and went on to become an icon of Pride in Spain. While male nudity was on full display and featured heavily in the media, there was little female nudity in the event.
The continuing process of commercializing Pride in 1996 caused some political tensions inside the LGT community, with Fundación Triángulo being founded as a moderate mixed gay and lesbian group in 1996 after splitting from COGAM partly in response to that tension. Despite being mixed, lesbian participation in Fundación Triángulo was at its start and continued to be well into the 2000s a minority participation.
Estimates for the number of people participating in Pride in 1997 vary dramatically, from three thousand to four thousand to five thousand to ten thousand people. It was also the first time Pride had a mascot, and commercially sponsored floats grew in number. Their presence was viewed as a victory by COGAM and businesspeople in Chueca, as it meant that Pride had managed to successfully grow from beyond its original core base of lesbian and gay militants. 
Pride 1998 continued along the same route that started in Puerta de Alcalá and ended in Puerta del Sol, taking place on the last Saturday of the month, 28 June. With ten thousand people participating, it was one of the biggest marches in years. The manifesto was read by Spanish singer and 1968 Eurovision winner Massiel, with the manifesto including demands for same-sex civil marriage.
Celebrating thirty years since the Stonewall riots in New York City, Pride in 1999 saw between 30,000 and 200,000 people participate in Pride and its connected activities in 1999, with the march route continuing its carnival type atmosphere between Puerta de Alcalá to Puerta del Sol. Male sexuality was firmly on display at this march, with many depictions of it in the print media. 
Alaska did her first concert at Pride in 1999 on the corner of Calle Augusto Figueroa and Pelayo as part of broader Pride celebrations organized by AEGAL. It was a free and attracted a lot of people, making it challenging for her in the future to repeat a street performance.
Change happened with Pride in the period between 2000 and 2020, with eight different routes and one cancellation, with the most frequent route being between the Puerta de Alcalá and the Plaza de España, passing through Gran Vía.
Chueca and its relationship with Pride was also changing during the early 2000s. As a result of the mass influx of people pouring into the area to celebrate in the period around Pride, streets were often pedestrianized. COGAM, who were getting subsidies from the local government to assist with the costs of organizing Pride, had started working with the townhall of Madrid to issue permits for parties in the area during Pride Week. COGAM’s cooperation with the city government was criticized by some LGTB militants as they felt it contributed to the commercialization of Orgullo at the expense of political goals of the LGBT movement.
A new and different lesbian culture was also starting to spring up around Pride in the early and mid-2000s, almost completely historically separated from the culture even fifteen years prior. It saw some lesbians organizing drag king workshops and producing lesbian centric porn in Spain and around Pride. By 2006, these lesbians were fully integrated into Madrid and Spain’s Pink Market. Some lesbian drag kings were critical of the commercialization of Pride in the city so integrated into Madrid Critical Pride events in instead.
Between seventy and one hundred thousand people marched on the 1.4 kilometer the 2000 Pride route between Puerta de Alcalá and Puerta del Sol. COGAM had once again convened the march, which featured a number of politicians leading it. Temperatures were in the 40Cs / 100Fc during most of Pride Week and during the march.
Adjacent activities to the main event included children’s parties, a film series, contests, concerts and festivals. Comisión 28 de junio, which was the integration of 15 homosexual collectives and 7 business associations in Chueca, organized the adjacent festivities. Institutional representatives of the local government and politicians were headquartered during the event on Calle Fuencarral, with the event having become important enough for them to need a location to coordinate their Pride messaging from.
Chueca again played an important role in Pride, with COGAM organizing a number of activities ending on 2 July 2000 in the neighborhood. Organizers went into the event optimistic about the potential economic impact of the event, believing that fifty to sixty thousand people would travel to the city from across Spain to participate. Organizers had hoped to run events in more locations across the city, but the Partido Popular run Junta Municipal de Centro banned Orgullo celebrations from taking place on Calles Augusto Figueroa, Pérez Galdós, Libertad, Infantas, San Marcos and Plaza de Vázquez de Mella, saying it would have too much of an effect on traffic and local residents. Organizers were informed of the ban on 23 June, only a few days before Pride Week was scheduled to start.
Pride got even bigger in 2001, with an estimated 150,000 people participating. At the same time, media attention of Pride started to shift from political demands or the protest nature of the event to increasingly focus on male sexuality, with many photos in the print media of barely clothed men, some in bondage type gear. The few pictures of women available at Pride in 2001 did not show them in sexualized outfits.
Pride participation more than doubled from the previous year, with an estimated 350,000 people participating in the march in 2002, one that followed the same route along Gran Vía. By 2003, this number had increased to half a million.
 (Fernández, 2018)
 (moscas de colores, 2014; Berzal de Miguel, 2020)
 Spanish: Ser gay no es suficiente”, afirmó González Zerolo. “Queremos pedir derechos perdidos para todos, más participación ciudadana ahora que el poder político se ha alejado de la calle y, también, más ludismo en estos tiempos de sainete”.
 Alaska is an icon of Spanish Pride. Alaska is an icon of Spanish Pride, and has had her own floats at a number of editions of the event in Madrid. She was one of the central figures of the Madrid Movida, and has sold some of the most records in Spain. (del Pozo, 2017)
 (Enguix Grau, “Nos defilamos, nos manifestamos”: Activismis y manifestaciones LGTB en España, 2017; moscas de colores, 2014)
 (Berzal de Miguel, 2020; moscas de colores, 2014; García J. , 2020)
 (Sainz, 2018; Berzal de Miguel, 2020; Sainz, 2018)
 (Berzal de Miguel, 2020; Sainz, 2018)
 (del Pozo, 2017)
 (Enguix Grau, “Nos defilamos, nos manifestamos”: Activismis y manifestaciones LGTB en España, 2017)
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