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The first maxi-singles
The term came into wide use in the 1980s, where it usually referred to 12" vinyl singles with 3 or 4 tracks. A typical practice was to release a 2-song single on 7" vinyl and cassette, and a maxi-single on 12" vinyl.
The early CD era
When CDs began to appear as a single format in the late 1980s (see CD single), songs were often released in two CD formats simultaneously, as a logical application of the vinyl record format to CD. There would be a regular single on a 3" CD with two tracks, similar to a 7" record. There would also be a full-size 5" CD, often with 3 or 4 tracks, which was considered the maxi-single despite often containing only marginally more music than its smaller counterpart.
Example: Erasure - Sometimes (European 5" CD maxi-single) Released by Mute in 1988 in Europe. Includes 3 different songs. Packaged in a slim jewel case with insert. Labelled "Maxi-Single-CD" on front cover.
Cassette maxi-singles
Occasionally, a cassette single would also be released in two cassette formats simultaneously: a traditional cassingle with two tracks and a cassette maxi-single with more tracks, generally remixes. This practice was experimented with in the early 1990s but was uncommon even then.
Example: Pet Shop Boys - So Hard (cassette maxi-single) Released by EMI in 1990 in the USA. Includes 3 mixes and one b-side. Packaged in a standard cassette case with "j-card" insert. Oddly, the spine calls it a "12 inch maxi-single" despite the fact that it's on a cassette.
1990s CD maxi-singles
Shortly after the advent of the 1990s, CD had clearly become the music format of choice. As the 1990s progressed, nearly every single released was available on CD, and vinyl and cassette single releases gradually became less common.
The UK became a thriving market for CD singles, but in 1998 the UK Chart Supervisory Committee reduced the maximum playing time of chart-eligible CD singles from 40 to 20 minutes, though 12" vinyl singles could still play for up to 40 minutes. While Maxi-CDs had been much loved among the dance community, as most if not all of the remixes that had been commissioned by the label could be released commercially, lobbying by artists in other genres who felt obliged to record extra and cover tracks to provide enough material for their single releases was to blame for the rule change. As a result, UK singles from the mid-1998 often appeared as 3 separately-sold CDs with 3 tracks each, or more commonly, 2 CDs and an extra format (such as 7", 12" or DVD single). Very often, at least 1 track was common to all formats. Single releases in the US and elsewhere still included many tracks (primarily remixes) and called themselves maxi-singles to differentiate from the 3-track UK versions.
Example: Saint Etienne - Who Do You Think You Are? (US CD single) Released by Warner Music in 1993 in the USA. Includes 8 different tracks, 6 of which are versions of the title song. Digipak packaging. Labelled "compact disc maxi-single" on the front cover.
Digital maxi singles
A digital maxi single is a series of digital downloads mostly containing remixes. Unlike a normal maxi single, tracks can be bought and sold based on preference. In terms of chart usage, even if a single had a maxi single and a digital maxi single released with the exact same content, they would still be counted differently. For instance, the maxi single would be counted as two points, while the digital maxi single (if all songs were downloaded and if the single were to contain the standard five tracks) would be counted as ten points.
The maxi-single today
With music stores in the US devoting increasingly less shelf space to singles, the format's future in the US remains in doubt. In the UK, having watched sales of CDs drop since the previous rule change, and amid allegations that the consumer no longer felt that UK issued singles were good value for money, the Chart Supervisory Committee once again changed the rules governing the formats of singles released in the UK. From early 2003, a format described as a "Maxi-CD" was again reintroduced, alongside a new 2-track CD single with a lower retail price. The current UK rules allow for up to 40 minutes of audio tracks on a Maxi-CD, as long as all tracks are remixes of the title track. In practice, however, many UK Maxi-CDs still contain only 3 mixes and come nowhere near the maximum allowable playing time. However, releases on dance labels (such as EMI's Positiva, for instance) are nearly always Maxi-CDs in the true sense, with more than 3 mixes.
Example: Erasure - Breathe (US CD single) Released by Mute in 2005 in the USA. Includes 8 different tracks, 6 of which are versions of the title song, plus a CD-ROM section with the video of the title song. Standard jewel case packaging.