Due to the experimental nature of Twitch Plays Pokemon at the onset, and because of initial low viewer counts as people were "discovering" TPP, very little record exists on what occured during this time.
Day 1, especially before 0d 9h, is largely unknown, with a viewer average of around 30-50 viewers for most of the day. The game started with the player character named RED and the rival character named BLUE. Red chose Charmander as his starter, and later, Oak's Parcel was delivered from Viridian City (which is also the location of the first ledge obstacle that the chat had trouble with). Red reached Pewter City after breezing through Viridian Forest. During this time, 4chan and then GBAtemp started picking up on the stream. Brock was defeated in a second try due to Abby having the attack Ember and better coordination with less players. For several hours after Brock's defeat, the small mob controlling Red, largely comprised of 4chan, struggled in Kanto Route 3 and Mt. Moon. A Pidgey, who would later become known as Bird Jesus, was caught on Route 3 during this time. The day ended with the IRC bot dying while the Streamer was sleeping, which led to the game being static for several hours.
After the Helix Fossil was obtained and Mt. Moon being cleared for the first time, Red blacked out after Abby was poisoned, before he could reach Cerulean City. This required the mob going through Mt. Moon again.
After finally reaching Cerulean City, the mob now had another challenge: Misty. Due to the Water type advantage over Fire, they struggled fighting Misty.
During this time, soon-to-be fan-favorite Pokémon Jay Leno was caught. Bird Jesus (Pidgey) evolved into Pidgeotto as well.
Misty was finally defeated after 8 hours of struggle and 11 tries, gaining Red his second badge.
The stream then moved on to save Bill from his teleportation mix up, inadvertently helping a character that would become the source of so much dread due to his creation of the PC system, famous for releasing Pokémon. Finally, another Rattata was added to the party, one that would soon earn his own name and place in history as Digrat. Red heads to his next destination: Vermilion City.
Around [01d 01h 09m]: Inputs working again, Red is unfrozen
Day 3 was mixed with ups and downs in terms of progress. While major characters were added, such as The Keeper and Dux, and Blue was defeated on S.S. Anne, players found themselves stuck at several trees that need to be cut for progress in the game. Successfully teaching Dux the Cut HM and getting him to cut these trees proved to be a great challenge for players. Luck turned in Lt. Surge's gym however, when the dreaded Trash Can Puzzle was solved with ease. Soon Surge was defeated and Red found himself with this third badge.
Day 4 could be called "Obstacle Day", as two major obstacles took up most of the day for the stream. Both the infamous Gen 1 ledge, also known as "The Ledge", and the Rock Tunnel, which had to be blindly cleared without any Pokemon with the ability Flash, took up large portions of the day. However, due to his exploits in carrying the party (often with only the move "Struggle", the default move when PP is out) through the Rock Tunnel, Bird Jesus began to cement himself as the messiah figure he would eventually be recognized as. The day ended on a triumphant note, as Red made it to Erika's Gym.
One of the most infamous days in Twitch Plays Pokemon history, day 5 began with a great win over Erika in which Bird Jesus shined, but things quickly took a downward turn for the community. First, while much of the community wished to keep a slot open in the part to eventually fill with Lapras for their surfing needs, Eevee was still obtained by Red. Players then opted to purchase a Water Stone to make a Vaporeon, but instead spent all of Red's money on 3 PokeDolls and a Fire Stone. Soon Eevee became a Flareon, and in the shuffle to try to reorganize the party in wake of this incident, two of the stream's most beloved Pokemon at this point were accidentaly released: Abby and Jay Leno. Utterly shocked, the community decided to press on into the Team Rocket HQ, only to find themselves fustratingly and hopelessly caught in the maze of spinning tiles. Even when progress was made, Digrat was accidentally ordered to use Dig from the START menu, taking Red back outside of the maze, negating any progress. As Day 5 drew to a close, the community began to seriously question if they were permanately stuck, and if this was the end of TPP.
As day 6 progressed with no end in sight for getting through the Team Rocket Headquarters, and Digrat earning some anger from community members for repeatedly digging Red back to the start of the maze, The Streamer soon took action to aid players by introducing Democracy mode [events completed under this mode now noted by '(D)']. Although many players did not like the change in the input system, progress began to be made, as the Lift Key was acquired and eventually Giovanni was reached. A new voting system for Anarchy and Democracy modes was introduced, marking the beginning of the major political schism of Gen 1. As word spread via news outlets concerning the crazy antics of TPP, soon new viewer-count highs were reached. The day ended with a loss to Giovanni.
Finally, after a full day-plus worth of play, a decisive victory by Bird Jesus and Dux sent Giovanni on his way and the Silph Scope was finally at hand! Well, until Digrat decided to Dig once again. Still, just a few hours later players were able to direct Red back to the Silph Scope and obtained it under Democracy mode. Meanwhile, the stream hit its all-time record for number of simultaneous players/viewers, breaking over 121 thousand. Red made his way to the Fighting Dojo, and players were excited for the potential of their new Hitmonlee, but he (along with X-Wing) were released not even forty minutes later. The day ended with Red entering the Pokémon Tower and catching Rick Gastly.
Known as "Ghost Hell", day 8 was full of antics in the Pokemon Tower. Players were having difficulty making progress as many of the Pokemon in the party did not have any moves that affected Ghost-types, but soon Digrat came to the rescue with Dig. This time Digrat used the move in battles, and it was very effective against the onslaught of dead Pokemon being faced, and the Raticate began to earn a lot of favor in the community. Finally, after several hours, Marowak (Cubone's mother)'s ghost was defeated and laid to rest, Mr. Fuji was saved, and Red came in possession of the Poké Flute. The day ends with Red proceeding south on Route 12 from Lavender Town to Fuchsia City.
After waking Snorlax, a short battle ensued before Red decided to run from combat. Still, on the journey to Fuchsia City, good progress was made on leveling team members, as Cabbage evolved and Bird Jesus became the first Pokemon on Red's roster to reach level 50. After a quick trip into the Safari Zone, the team was able to beat Koga before turning their sights back onto the Safari Zone. It didn't take long for players to realize the danger inherent in trying to tackle the zone, as the step count was still active (despite previous rumours that it had been deactivated), and Red had limited funds. This marked the most extensive use of Democracy mode to date, as players worked together via voting on commands to carefully make their way to the hidden house in the back of the zone to obtain Surf. While in the Safari Zone a total of thirteen Pokemon were caught, including fan-favorites and hall of famers The Fonz and ATV. After obtaining Surf and a bit of PC antics (no releases this time), Red made his way to defeat Blue before adding another legend of Gen 1 to his team, Air Jordan.
Day 10 did not see as many major events as others, which is fitting considering it is sandwiched between two very eventful days. Progress was made though, first with the conquering of Giovanni in the Silph Company HQ to obtain the Master Ball, and the on to Sabrina's Gym. Sabrina's Gym was a challenge for the stream, as navigating the teleporting pads under Anarchy mode proved to be quite the puzzle. Sabrina defeated the team once, before Red was able to be directed back to her by players. Bird Jesus carried the team again, further adding to his legacy with a solid win over Sabrina for the badge.
The most infamous day in all of Twitch Plays Pokemon history, day 11 of Gen 1, also known as "Bloody Sunday", started off on a high note as players made their way through the Power Plant and managed to capture the legendary Zapdos (AA-j) with the Master Ball in Anarchy mode. Seeking to bring AA-j into the active party, Red was directed to the PC in the Power Plant. What followed was some of the most chaotic several hours in TPP history. Shuffling occured between active and PC Pokemon as attempts were made to build the team around both Bird Jesus and AA-j, while keeping HM users such as Dux on the active team as well. Unfortunately, coordination under Anarchy mode can be difficult and releasing Pokemon via the PC in Gen 1 was a fairly easy thing to do. By day's end, a total of twelve Pokemon were released, including fan-favorites Cabbage and Digrat, and the loved Dux, which meant that there was no longer a mon on the team that knew Cut. This left the stream helpless but to reenter the Rock Tunnel, still lacking the Flash HM, and brave it in the dark again. Bird Jesus was able to carry the team through the dark tunnel, often by using "Struggle" after he ran out of PP, and as the day closed the community sat in shock and asked if AA-j was worth the losses that had occurred.
[10d 04h 34m]: Destiny, an online streamer who is planning to use Democracy mode to release Red's best Pokémon, joins Twitch Plays Pokémon. He and his followers immediately begin mass-voting for Democracy
[10d 04h 47m] (D): Democracy mode activated
[10d 04h 54m] (D): People begin to inform others about Destiny's plan to ruin the stream, Unathana posts a Reddit thread about Destiny 
Because of the loss of Dux, the team had to backtrack through Mt. Moon and Pallet Town to reach Cinnabar Island. Along the way players stopped by the Day Care, and Rick Gastly was left there for the remainder of the run. Day 12 marked the first visit back to Red's hometown since day 1 of play. After reaching Cinnabar, the Helix Fossil was taken to the laboratory to be revived. After a PC shuffle that resulted in the loss of a few Pokemon, Lord Helix was officially brought onto the active party, with The Keeper taking his place in the PC. This marked the last time in the run any Pokemon was either deposited or withdrawn from the PC. With the community rejoicing around the revival of Helix, and the final party set for the remainder of the game, players set out to take on Pokemon Mansion. After a battle with the NPC Burglar Simon, Red became stuck in a one by two space between the NPC, a table, and the wall. Players spent the rest of the day roaming this small space engaging in random encounters, until finally all active Pokemon fainted and Red was transported to the Pokecenter outside.
After finally getting out from being trapped by the Burglar, Surf was taught to both Lord Helix and The Fonz, before players trekked back into Pokemon Mansion. After some more dealings with the secret switch puzzles inside the Mansion, the stream was finally able to obtain the Secret Key that gives access to Blaine's Gym. In the battle that ensued against Blaine, the gym leader was made short work of with AA-j quickly ending the battle in just six moves. Red journeyed back up to Pallet Town, stopped by his house, and then found his way up to Viridian City, with his eye's set on Giovanni.
One of the harder late-game obstacles was faced on this day as players attempted to navigate Red through the small space between the front of the Viridian City gym and the ledge that was only one space away. The ledge was hopped several times, causing Red to have to circle back around the gym to make another attempt. Even after successfully navigating the obstacle a few times, Red would often enter the gym and then accidently exit it and jump the ledge again. Frustration arose in the community and calls for Democracy mode could be heard, but after several attempts, a few lessons on how to catch Weedles from a friendly NPC, and some patience, players finally successfully cleared the ledge and made their way to Giovanni. Giovanni won the first fight, but in the second attempt Bird Jesus shined after burying Giovanni's Rhydon in Sand Attacks. Soon, the gym leader's Pokemon was unable to land an attack, and with low HP Bird Jesus was able to finally land the knock-out blow. Afterwards, Red made his way to the entrance of Victory Road, where he faced Blue and defeated him. The day ends with grinding at Pokémon Mansion beginning.
After a few attempts to get past the ledge west of Viridian City at the entrance of Victory Road, an operation was born that sent the team back down to Cinnabar to 'grind' the active Pokemon to higher levels in the Pokemon Mansion. After several hours, the stream took Red back up to Victory Road. The ledge was cleared, but not long after entering Victory Road the team blacked out. Because Cinnabar was the last place the team healed at, the checkpoint was set for there, and the stream found itself back on the southern island. Players decided to take advantage and reenter the Mansion, where they spent several more hours in random encounter battles. Soon Lord Helix evolved into an Omastar, and the "Day of Grinding" came to a close.
Day 16 took Red back to Victory Road, and after the addition of key moves such as Sky Attack and Strength to party-member's movesets thanks to a run in Democracy mode, players set out to conquer the giant cave system and make it to the Pokemon League. The moving of boulders to allow for progress proved to be challenging in Anarchy mode, and soon Democracy was initiated to help clear the levels of Victory Road. After several hours, Red finally reached the Pokemon League, and took on Lorelei for the first time. Lorelei triumphed several times over the team before the stream managed to beat her. Each member of the Elite Four brought its own challenge to the team, and players spent the rest of the day attempting and reattempting to defeat the Elite Four. Still, legends were born, as ATV became known as the "Dragon Slayer" after he single-handedly beat Lance's Dragonite who was around twenty levels higher than him, and the stream managed to reach champion Blue before falling quickly to him. The day ended back at the Pokecenter healing, but excitement could be felt through-out the community as the end-game was at hand.
VICTORY! After seventeen attempts, Red made it past Lance for a second time and reached Blue again. This time, more than just ATV remained active in the party, including the powerhouse AA-j. As 'a' commands rained in through the streams chat, AA-j used a final Thunder on Blue's Blastoise, knocking out the water Pokemon, and Red became champion. After 16 days, seven hours, 45 minutes and 30 seconds, the community had defeated Pokemon Red.