PokéBase - Pokémon Q&A
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For dress-up. Maybe how many.

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Best answer

Backdrop Location

Dress Up
Obtained with Fashion Case.

Ranch
Possible default obtained with Fashion Case.
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

City at Night
Possible default obtained with Fashion Case.
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Snowy Town
Possible default obtained with Fashion Case.
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Fiery
Possible default obtained with Fashion Case.
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Outer Space
Possible default obtained with Fashion Case.
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Cumulus Cloud
Possible default obtained with Fashion Case.
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Desert
Possible default obtained with Fashion Case.
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Flower Patch
Possible default obtained with Fashion Case.
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Future Room
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Open Sea
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Total Darkness
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Tatami Room
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Gingerbread Room
Match the first digit from the right in the Jubilife TV Pokémon Lottery Corner.DP
Receive from a woman on the first floor of the Global Terminal.Pt
Receive from a man in the Goldenrod Tunnel.HGSS

Seafloor
Pal Park (Sapphire in the GBA slot)

Underground
Pal Park (Ruby in the GBA slot)

Sky
Pal Park (Emerald in the GBA slot)

Theater
Unknown method

From http://bulbapedia.bulbagarden.net/wiki/Backdrop

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for hg/ss in goldenrod tunnel are those from the lottery in the picture room with the hiker?
Yep. :D
(spending 4 hours on heartgold getting all of the backgrounds)