For companies that value innovation, money has never been an object standing in the way of advancement. This is especially true among technology companies, where routinely high valuations drive purchase prices well into the billions of dollars.

Let’s take a look at 10 of the biggest tech acquisitions of all time.

1. AOL buys Time Warner, $106 billion

Thinking of AOL as a separate company may seem like a distant memory since it essentially got swallowed up by Time Warner (rather than vise versa), but this acquisition represented the peak of dot-com excess. The merger was announced in 2000, and the price tag was initially $165 billion, due to a high market capitalization, but the burst of the dot com bubble quickly cut down that price by the time the deal closed. Still, this deal happened at the last possible second that the market would accept a +$100 billion deal, and tech stocks collapsed soon after.

Sound off in the comments if you still have any free AOL internet CDs.

2. Facebook buys WhatsApp, $19 billion

Cleared earlier this year, the $19 billion Facebook acquisition of WhatsApp represents the largest exit of a venture capital-backed company in history. WhatsApp allows users to send mobile messages to one another, and the acquisition was met with criticism from some privacy groups who saw the potential for user data to be monetized by Facebook.

3. HP buys Compaq, $18.6 billion

As recommended by John Cleese’s brother-in-law in the late 1980s, Compaq computers were a force to be reckoned with. In the early 2000s, however, the brand began to falter and fellow giant HP began looking for a way to capture it. The acquisition was initially announced in June 2001 at a higher price tag, but HP closed the deal in May 2002 for close to $19 billion. The deal was at the time, and remains the biggest computer hardware deal in history.

4. HP buys EDS, $13.9 billion

In late August 2008, HP completed the purchase of Electronic Data Systems Corporation (EDS) for nearly $14 billion. EDS was a multinational company started by Ross Perot and headquartered in Plano, Texas. EDS was known for building an automatic code generator and a system for allowing ATMs to take money, but HP bought it for its IT services business. The current corporate entity is referred to as HP Enterprise Services.

5. Symantec buys Veritas, $13.5 billion

In the middle of 2005, security software company Symantec finalized its purchase of Veritas, a company focused on storage management known for creating the first commercial journaling file system. Not only did the deal give Symantec a slew of new product offerings from Veritas, but it also afforded access to the Veritas list of Fortune 500 company clients.

6. Google buys Motorola Mobility, $12.5 billion

In 2012, Google made its first step towards becoming a hardware company when it completed its acquisition of Motorola Mobility. The purchase was by far Google’s largest to date at the time, but the company has since struggled to compete in the hardware space. Google recently unloaded part of Motorola Mobility for $2.9 billion, leading many to question why Google even bought it in the first place.

7. Oracle buys PeopleSoft, $10.3 billion

After a year and a half struggle, Oracle closed on its acquisition of PeopleSoft in January 2005. The hostile takeover was originally rejected by PeopleSoft, but it eventually agreed to the merger; making Oracle second only to SAP at the time for business software.

8. HP buys Autonomy, $10.3 billion

In October 2011, 87% of Autonomy’s shareholders agreed to $10.24 billion deal to be acquired by HP. Autonomy is a UK company whose products came from research performed at the University of Cambridge. The majority of Autonomy’s products were based on Bayesian inference and were geared toward the enterprise. The company is now known as HP Autonomy.

9. Microsoft buys Skype, $8.5 billion

In 2011 video calls were taking off and Skype was leading the charge. When European regulators cleared the deal in late 2011, it became official that Microsoft purchased the company. eBay first acquired Skype in 2005 and the company was later sold to a group led by Silver Lake Partners in 2009 before landing at Microsoft.

10. Oracle buys Sun Microsystems, $7.4 billion

Perhaps one of the most strategic purchases Oracle has made was to acquire Sun Microsystems. Oracle paid cash for Sun which, at the time, was a struggling company. The acquisition gave Oracle ownership over both the Java programming language and the Solaris operating system.