Released with Edward and in the first Thomas the Tank Engine and Freight Cars Set in 1996, Troublesome Trucks are a staple of the Thomas series and were widely used in the Thomas Plarail series with a variety of faces and colors in the following decades. The original 1996 face (far left) is considered the "laughing" face.
The chassis for these trucks was initially dated 1996 with the bottom line of licensing text offset to the left. Very early examples use the older style of single-split couplings. Around 1999 a ring was added around the screw holding the truck together. Around 2000 a new tooling with more centered 1996 licensing information was introduced.
In 2002 the later 1996-dated chassis was updated instead to say 2002, with visible lines where the tooling was changed. This tooling was later updated with the new squared-off Tomy logo and used in the early 2000s, with an additional similar set of molds being produced with the 2002 date and straight Tomy logo from their inception being used as the Thomas series continued to expand and sell overseas. Both of these toolings were in use in the mid 2000s.
Beginning with Lady and Diesel 10 in 2000, several color variations of different trucks have been produced including black, dark green, a few shades of blue, orange, and others.
In the Thomas stories, S.C. Ruffy is a privately-owned truck that is rotting away in the sidings when Oliver ends up pulling him apart, prompting his rebuild. The original orange-chassis S.C. Ruffy representing his initial appearance was released with the Plarail Duck in May 1997, making it the first variation of the Troublesome Truck after the original (even predating any of the regular truck's face variations).
First released in the 2001 Thomas and Busy Freight Cars Set, a darker brown "rebuilt" version of S.C. Ruffy was also produced, making its way into some export sets as well as the European Motor Road & Rail Diesel, Freight Wagons, and Cargo train pack.
In 2004 the 2002 licensing information scrappy S.C. Ruffy was released individually in hanging plastic boxes in the United States.
Also released in 1996 and using the same chassis as the Troublesome Truck is this Troublesome Van based on vans seen in the television series. This is a nice van with a face sticker on the rear but unfortunately unlike the troublesome truck no other face variations were released.
As it uses the same chassis as the troublesome trucks, it went through similar chassis revisions.
This tooling was occasionally used without a face, such as in red with Neville.
In 2000 this not-for-sale two-pack of the original laughing face Troublesome Truck and Troublesome Van was released in Japan as Plarail Troublesome Trucks (いじわる貨車). The exact way this pack was acquired is currently unknown, as the packaging does not make any specific mention of a contest or prize, and the entire rest of the box is blank.
These cars actually have production stickers dating them to March 2000, unlike most other rolling stock. In the early 2000s Tomy put these production stickers, previously reserved for battery-powered trains and accessories, on some individual rolling stock and unpowered accessory releases. Without the box, these stickers are probably the only way to tell cars that came from one of these packs apart from other random trucks of the era.
In 2004 in the United States the troublesome van was released individually as Troublesome Truck #2.
Initially released alongside S.C.Ruffy with Plarail Duck in May 1997, Toad the Great Western Railways brakevan uses the same chassis as other troublesome trucks (although Toad is not particularly troublesome, and is an ally to Oliver and the other Sodor steam engines, unlike some other brake vans).
In 2004 in the United States Toad was released individually as Troublesome Truck #1.
As part of a series of individual Thomas-series freight cars released in March 2006, a dark green truck was released with two fruit loads as みどりいろの貨車 Green Freight Car. The boxes for these cars were individual hang-tag style and were sold for a few years. This one has been opened at some point and re-taped but I don't really have a reason to open it again - I have come across two others of these dark green trucks.
The truck has the "angry" face.
The chassis for these individual releases were marked with a production period - B06 signifying February 2006 means these two examples are fairly early production.
As part of a series of individual Thomas-series freight cars released on March 9th, 2006 a light blue was released with two bluish pieces of rock cargo from the same tooling as the original clay loads as あおいろの貨車 Blue Freight Car.
These wagons have nice highlighted bracing, which makes them stand out even more from other trucks. By the time of these example's production in 2007, the day of the month was also included in the production stamps.
On March 9th, 2006 a dark brown troublesome truck with sad face and two dark brown barrel loads as ちゃいろの貨車 Brown Freight Car.
In 2007, first with Duncan, a slate wagon representing those seen in the Thomas series was produced with the same chassis and nominal inner dimensions as the troublesome trucks, meaning they are cross-compatible with the drop-in loads (introducing slate loads at the same time).
Different trains, train packs, and even sets occasionally included different color variations with different loads.
Included in the Percy and Pounding Wagons Set was this geared Rattling Freight Car (がたがた貨車) that propels the crates inside up and down as it rolls. This car was used in a few other Thomas-series train packs.
Also included in the Percy and Pounding Wagons Set in 2007 was the Wobbly or Shaky Freight Car (ぐらぐら貨車), which has off-center wheels with plastic tread to make the truck rock from side to side as it rolls.
Like the truck with crates, the rocking truck was included in a few other train packs and even in a neat set with a Thomas that can go backwards.